A Polyketide Male-Produced Aggregation-Sex Pheromone Shared by the North American Cerambycid Beetle Graphisurus fasciatus and the South American Cerambycid Eutrypanus dorsalis

Kyle Arriola; Weliton D Silva; Lawrence M Hanks; Linnea R Meier; Jocelyn G Millar

doi:10.1007/s10886-024-01505-x

A Polyketide Male-Produced Aggregation-Sex Pheromone Shared by the North American Cerambycid Beetle Graphisurus fasciatus and the South American Cerambycid Eutrypanus dorsalis

J Chem Ecol. 2024 May 13. doi: 10.1007/s10886-024-01505-x. Online ahead of print.

Authors

Kyle Arriola^{1

2}, Weliton D Silva³, Lawrence M Hanks⁴, Linnea R Meier⁴, Jocelyn G Millar⁵

Affiliations

¹ Department of Entomology, University of California, 900 University Ave, Riverside, CA, 92521, USA.
² Department of Chemistry, MiraCosta College, Building OC 3600, 1 Barnard Drive, Oceanside, CA, 92056, USA.
³ Department of Entomology and Acarology, University of Sao Paulo, Piracicaba, SP, 13418900, Brazil.
⁴ Department of Entomology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA.
⁵ Department of Entomology, University of California, 900 University Ave, Riverside, CA, 92521, USA. millar@ucr.edu.

PMID: 38739335
DOI: 10.1007/s10886-024-01505-x

Abstract

The longhorn beetle Graphisurus fasciatus (Degeer) ranges from southeastern Canada to Florida and west to Texas, and has frequently been caught during field trials testing attraction of other cerambycid species to their synthesized pheromones. Collections of headspace volatiles from live beetles revealed that males but not females produce a polyketide compound identified as (4R,6S,7E,9E)-4,6,8-trimethylundeca-7,9-dien-3-one ([4R,6S,7E,9E]-graphisurone). Field trials verified that beetles of both sexes were attracted to the synthesized compound, indicating that it is an aggregation-sex pheromone. This structure represents a new structural motif among cerambycid pheromones, and a new natural product. While this study was in progress, the same compound was isolated from males of the South American cerambycid Eutrypanus dorsalis (Germar), in the same subfamily (Lamiinae) and tribe (Acanthocinini) as G. fasciatus. Field trials in Brazil confirmed that (4R,6S,7E,9E)-graphisurone is also an aggregation-sex pheromone for E. dorsalis, and a possible pheromone for two additional sympatric lamiine species, Hylettus seniculus (Germar) (Acanthocinini) and Oreodera quinquetuberculata (Drapiez) (tribe Acrocinini). These results indicate that graphisurone may be shared among a number of related species, as has been found with many components of cerambycid pheromones.

Keywords: Aggregation-sex pheromone; Cerambycidae; Invasive species; Longhorned beetle.

Abstract

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