Journal of Chemical Ecology

, Volume 41, Issue 5, pp 465–472

N-3-Methylbutanoyl-O-methylpropanoyl-L-serine Methyl Ester – Pheromone Component of Western Black Widow Females

  • Catherine Scott
  • Sean McCann
  • Regine Gries
  • Grigori Khaskin
  • Gerhard Gries
Article

DOI: 10.1007/s10886-015-0582-x

Cite this article as:
Scott, C., McCann, S., Gries, R. et al. J Chem Ecol (2015) 41: 465. doi:10.1007/s10886-015-0582-x

Abstract

Chemical communication is common in spiders but few pheromones have been identified. Female widow spiders in the genus Latrodectus spin webs that disseminate an attractive sex pheromone, and a contact pheromone on the silk elicits courtship behavior by males. The methyl ester of N-3-methylbutanoyl-O-(S)-2-methylbutanoyl-L-serine is a contact pheromone of the Australian redback spider Latrodectus hasselti. We hypothesized that the contact pheromone of congeneric L. hesperus resembles that of L. hasselti. The silk of virgin L. hesperus females was extracted with methanol, and analyses by gas chromatography–mass spectrometry (GC/MS) provided evidence for the presence of N-3-methylbutanoyl-O-methylpropanoyl-L-serine methyl ester (MB-MP-S), a lower homologue of the L. hasselti contact pheromone. Behavioral responses of L. hesperus males to test stimuli were assayed on T-shaped rods with the end sections of the horizontal arm enveloped in filter paper. Males spent 40 % longer in contact with paper bearing female silk than with blank paper, and 39 % longer in contact with paper treated with silk extract than with solvent controls. Contact with silk and silk extract induced courtship behavior by 96 % and 80 % of males, respectively, indicating that there was a methanol-soluble courtship-eliciting contact pheromone on the silk. Males responded less strongly to synthetic MB-MP-S than to silk or silk extract. Paper impregnated with synthetic MB-MP-S (10 or 100 μg) induced courtship behavior in 3–16 % of males, and prompted males to stay 10–16 % longer than on control paper. Our data support the conclusion that MB-MP-S is part of a multi-component contact pheromone of L. hesperus.

Keywords

Latrodectus Chemical communication Pheromone Amino acid Silk Courtship 

Supplementary material

10886_2015_582_MOESM1_ESM.doc (154 kb)
ESM 1General methods and instrumentation for syntheses, a representative synthesis of ester-amide mixtures, and synthesis of N-3-methylbutanoyl-O-methylpropanoyl-L-serine methyl ester (DOC 153 kb)
View video
ESM 2

A Latrodectus hesperus male silk-wrapping a filter paper treated with methanol extract of a virgin female’s web, first at normal speed, then slowed to half-speed (MP4 12085 kb)

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Catherine Scott
    • 1
  • Sean McCann
    • 1
  • Regine Gries
    • 1
  • Grigori Khaskin
    • 1
  • Gerhard Gries
    • 1
  1. 1.Department of Biological SciencesSimon Fraser UniversityBurnabyCanada