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.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Tax calculation will be finalised during checkout.
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
Tax calculation will be finalised during checkout.
Andrade M, Kasumovic M (2005) Terminal investment strategies and male mate choice: extreme tests of Bateman. Integr Comp Biol 45:838–47. doi:10.1093/icb/45.5.838
Arn H, Städler E, Rauscher S (1975) The electroantennographic detector—a selective and sensitive tool in the gas chromatographic analysis of insect pheromones. Z Naturforsch 30c:722–725
Blumstein DT, Daniel JC, Evans CS (2012) Jwatcher. Available online: http://www.jwatcher.ucla.edu/
Chinta SP, Goller S, Lux J, Funke S, Uhl G, Schulz S (2010) The sex pheromone of the wasp spider Argiope bruennichi. Angew Chem Int Ed 49:2033–2036. doi:10.1002/anie.200906311
Gaskett AC (2007) Spider sex pheromones: emission, reception, structures, and functions. Biol Rev Camb Philos Soc 82:27–48. doi:10.1111/j.1469-185X.2006.00002.x
Hebets EA, Chapman RF (2000) Electrophysiological studies of olfaction in the whip spider Phrynus parvulus (Arachnida, Amblypygi). J Insect Physiol 46:1441–1448. doi:10.1016/S0022-1910(00)00068-8
Jerhot E, Stoltz JA, Andrade MCB, Schulz S (2010) Acylated serine derivatives: a unique class of arthropod pheromones of the Australian redback spider, Latrodectus hasselti. Angew Chem Int Ed 49:2037–2040. doi:10.1002/anie.200906312
Kasumovic M, Andrade MCB (2004) Discrimination of airborne pheromones by mate-searching male western black widow spiders (Latrodectus hesperus): species- and population-specific responses. Can J Zool 82:1027–1034. doi:10.1139/z04-081
MacLeod EC, Andrade MCB (2014) Strong, convergent male mate choice along two preference axes in field populations of black widow spiders. Anim Behav 89:163–169. doi:10.1016/j.anbehav.2013.12.023
Papke MD, Riechert SE, Schulz S (2001) An airborne female pheromone associated with male attraction and courtship in a desert spider. Anim Behav 61:877–886. doi:10.1006/anbe.2000.1675
Prouvost O, Trabalon M, Papke M, Schulz S (1999) Contact sex signals on web and cuticle of Tegenaria atrica (Araneae, Agelenidae). Arch Insect Biochem Physiol 40:194–202. doi:10.1002/(SICI)1520-6327(1999)40:4<194::AID-ARCH4>3.0.CO;2-P
R Core Team (2013) R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, URL http://www.r-project.org/
Ross K, Smith RL (1979) Aspects of the courtship behavior of the black widow spider, Latrodectus hesperus (Araneae: Theridiidae), with evidence for the existence of a contact sex pheromone. J Arachnol 7:69–77
Schulz S (2013) Spider pheromones – a structural perspective. J Chem Ecol 39:1–14. doi:10.1007/s10886-012-0231-6
Schulz S, Toft S (1993) Identification of a sex pheromone from a spider. Science 260:1635–1637. doi:10.1126/science.260.5114.1635
Scott C, Vibert S, Gries G (2012) Evidence that web reduction by western black widow males functions in sexual communication. Can Entomol 144:672–678. doi:10.4039/tce.2012.56
Stoltz JA, McNeil JN, Andrade MCB (2007) Males assess chemical signals to discriminate just-mated females from virgins in redback spiders. Anim Behav 74:1669–1674. doi:10.1016/j.anbehav.2007.03.011
Tichy H, Gingl E, Ehn R, Papke M, Schulz S (2001) Female sex pheromone of a wandering spider (Cupiennius salei): identification and sensory reception. J Comp Physiol A 187:75–78. doi:10.1007/s003590000175
Trabalon M, Niogret J, Legrand-Frossi C (2005) Effect of 20-hydroxyecdysone on cannibalism, sexual behavior, and contact sex pheromone in the solitary female spider, Tegenaria atrica. Gen Comp Endocrinol 144:60–6. doi:10.1016/j.ygcen.2005.04.011
Uhl G, Elias DO (2011) Communication. In: Herberstein ME (ed) Spider behaviour: flexibility and versatility. Cambridge University Press, Cambridge, pp 127–189
Van den Dool H, Kratz P (1963) A generalization of retention index system including linear temperature programmed gas–liquid partition chromatography. J Chromatogr A 11:463–471. doi:10.1016/S0021-9673(01)80947-X
Xiao Y, Zhang J, Li S (2010) Male-specific (Z)-9-tricosene stimulates female mating behaviour in the spider Pholcus beijingensis. Proc R Soc B Biol Sci 277:3009–3018. doi:10.1098/rspb.2010.0763
Xiao Y, Zhang J, Li S (2009) A two-component female-produced pheromone of the spider Pholcus beijingensis. J Chem Ecol 35:769–778. doi:10.1007/s10886-009-9660-2
We thank the Tsawout First Nation for permission to do field work on their lands, the Capital Regional District for granting permits to collect spiders from Island View Beach; Maydianne Andrade, Bernard Roitberg, Tanya Stemberger, Samantha Vibert, and two anonymous reviewers for comments that improved the manuscript; Huimin Zhai for comments on the chemistry section; and Susan Chen and Elaine Wu for assistance with spider rearing and maintenance. Funding was provided by a Natural Sciences and Engineering Research Council of Canada (NSERC) – Discovery Grant and an NSERC – Industrial Research Chair to G.G., with Contech Enterprises Inc. and Global Forest Science as industrial sponsors.
Electronic Supplementary Material
Below are the links to the electronic supplementary material.
General 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)
About this article
Cite this article
Scott, C., McCann, S., Gries, R. et al. N-3-Methylbutanoyl-O-methylpropanoyl-L-serine Methyl Ester – Pheromone Component of Western Black Widow Females. J Chem Ecol 41, 465–472 (2015). https://doi.org/10.1007/s10886-015-0582-x
- Chemical communication
- Amino acid