Pheromone Composition and Chemical Ecology of Six Species of Cerambycid Beetles in the Subfamily Lamiinae

Linnea R. Meier, Yunfan Zou, Judith A. Mongold-Diers, Jocelyn G. Millar, Lawrence M. Hanks

Research output: Contribution to journalArticle

Abstract

Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes.

Original languageEnglish (US)
Pages (from-to)30-39
Number of pages10
JournalJournal of Chemical Ecology
Volume46
Issue number1
DOIs
StatePublished - Jan 1 2020

Fingerprint

chemical ecology
Pheromones
Beetles
Ecology
pheromone
pheromones
beetle
enantiomers
acetates
acetate
Acetates
Coleoptera
Enantiomers
Chemical analysis
acetate (ester)
aggregation pheromone
aggregation pheromones
chemical speciation
sex pheromone
Sex Attractants

Keywords

  • Antagonism
  • Attractant pheromone
  • Geranylacetone
  • Longhorned beetle
  • Sulcatone
  • Terpenoids

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Cite this

Pheromone Composition and Chemical Ecology of Six Species of Cerambycid Beetles in the Subfamily Lamiinae. / Meier, Linnea R.; Zou, Yunfan; Mongold-Diers, Judith A.; Millar, Jocelyn G.; Hanks, Lawrence M.

In: Journal of Chemical Ecology, Vol. 46, No. 1, 01.01.2020, p. 30-39.

Research output: Contribution to journalArticle

Meier, Linnea R. ; Zou, Yunfan ; Mongold-Diers, Judith A. ; Millar, Jocelyn G. ; Hanks, Lawrence M. / Pheromone Composition and Chemical Ecology of Six Species of Cerambycid Beetles in the Subfamily Lamiinae. In: Journal of Chemical Ecology. 2020 ; Vol. 46, No. 1. pp. 30-39.
@article{8d68a7e004924e2eb42dd0dc084b4b8d,
title = "Pheromone Composition and Chemical Ecology of Six Species of Cerambycid Beetles in the Subfamily Lamiinae",
abstract = "Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes.",
keywords = "Antagonism, Attractant pheromone, Geranylacetone, Longhorned beetle, Sulcatone, Terpenoids",
author = "Meier, {Linnea R.} and Yunfan Zou and Mongold-Diers, {Judith A.} and Millar, {Jocelyn G.} and Hanks, {Lawrence M.}",
year = "2020",
month = "1",
day = "1",
doi = "10.1007/s10886-019-01128-7",
language = "English (US)",
volume = "46",
pages = "30--39",
journal = "Journal of Chemical Ecology",
issn = "0098-0331",
publisher = "Springer New York",
number = "1",

}

TY - JOUR

T1 - Pheromone Composition and Chemical Ecology of Six Species of Cerambycid Beetles in the Subfamily Lamiinae

AU - Meier, Linnea R.

AU - Zou, Yunfan

AU - Mongold-Diers, Judith A.

AU - Millar, Jocelyn G.

AU - Hanks, Lawrence M.

PY - 2020/1/1

Y1 - 2020/1/1

N2 - Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes.

AB - Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes.

KW - Antagonism

KW - Attractant pheromone

KW - Geranylacetone

KW - Longhorned beetle

KW - Sulcatone

KW - Terpenoids

UR - http://www.scopus.com/inward/record.url?scp=85076217897&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85076217897&partnerID=8YFLogxK

U2 - 10.1007/s10886-019-01128-7

DO - 10.1007/s10886-019-01128-7

M3 - Article

AN - SCOPUS:85076217897

VL - 46

SP - 30

EP - 39

JO - Journal of Chemical Ecology

JF - Journal of Chemical Ecology

SN - 0098-0331

IS - 1

ER -