Identification, synthesis, and bioassay of a male-specific aggregation pheromone from the harlequin bug, Murgantia histrionica.

Journal of Chemical Ecology
Deane K ZahnJocelyn G Millar

Abstract

Sexually mature male harlequin bugs produced a sex-specific compound, identified as one of the stereoisomers of the sesquiterpene epoxyalcohol 4-[3-(3,3-dimethyloxiran-2-yl)-1-methylpropyl]-1-methylcyclohex-2-en-1-ol (henceforth murgantiol), a compound with four chiral centers and 16 possible stereoisomers. Production of the compound was highest during the middle of the day. Individual virgin male bugs in separate containers produced the compound at a higher rate than virgin males in groups. The carbon skeleton was verified by synthesis of several mixtures which, in total, contained all possible isomers, one of which matched the insect-produced compound. The relative and absolute configurations of the insect-produced compound remain to be determined. In laboratory bioassays, insect-produced and synthetic murgantiol attracted harlequin bugs of both sexes, suggesting that murgantiol is a male-produced aggregation pheromone, analogous to those found in a number of other phytophagous bug species.

References

Sep 8, 2001·Journal of Chemical Ecology·H L McBrienR E Rice
Nov 5, 2002·Annual Review of Entomology·Andrej Cokl, Meta Virant-Doberlet
Nov 27, 2002·Journal of Chemical Ecology·Alireza AliabadiDouglas W Whitman
Nov 8, 2006·Journal of Chemical Ecology·Miguel BorgesMaria C B Moraes

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Citations

Jun 14, 2012·Journal of Chemical Ecology·Paulo H G ZarbinMauro A C M Rodrigues
Nov 26, 2015·Journal of Natural Products·Ashot KhrimianFiladelfo Guzman
Sep 1, 2015·Journal of Chemical Ecology·Carla F FávaroPaulo H G Zarbin
Nov 20, 2014·Journal of Chemical Ecology·Ashot KhrimianDonald C Weber
Oct 6, 2017·Journal of Economic Entomology·Anthony S DiMeglioDonald C Weber
Sep 30, 2018·Journal of Chemical Ecology·Jason LancasterDorothea Tholl
Aug 25, 2018·Proceedings of the National Academy of Sciences of the United States of America·Jason LancasterDorothea Tholl

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