Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis

J Nat Prod. 2022 Aug 26;85(8):2062-2070. doi: 10.1021/acs.jnatprod.2c00470. Epub 2022 Jul 25.

Abstract

The leaffooted bugs Leptoglossus zonatus and L. occidentalis (Hemiptera: Coreidae) cause substantial damage in tree nut crops in North America and pine seed orchards in North America and Europe, respectively. Sexually mature males of both species produce a number of aldehydes, esters, and sesquiterpenes, which are hypothesized to constitute an aggregation pheromone attractive to both sexes. Among the volatiles produced by males of both species, we identified a unique sesquiterpene hydrocarbon, given the common name "leptotriene" (5), which elicited strong responses from antennae of both sexes in electroantennogram assays. Here, we report its structure and its synthesis from (-)-(E)-β-caryophyllene (1).

Publication types

  • Review
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Female
  • Heteroptera*
  • Male
  • Pinus*
  • Seeds
  • Sesquiterpenes*

Substances

  • Sesquiterpenes