Acylated Serine Derivatives: A Unique Class of Arthropod Pheromones of the Australian Redback Spider, Latrodectus hasselti

摘要

Spiders are of great ecological importance, as they are the major predators of terrestrial insects. Many species use chemical communication along with other cues during courtship, but these systems are not well investigated, especially compared to other arthropods, such as insects or mites. Spiders commonly make use of silk; mate attraction, initiation of courtship, and other critical aspects of spider reproduction are apparently triggered by pheromones on the silk or the body of the female. Most of the handful of spider pheromones that have been identified are structurally different from those known from insects. Herein, we report the identification of the unusual methyl ester of N-3-methylbutyryl-O-(S)-2-methylbutyryl-L-serine 3 as a female sex pheromone of the Australian redback spider, Latrodectus hasselti. This compound represents a new class of secondary metabolites, N,O-diacylated serine derivatives.