Location: Chemistry Research Unit
Title: Glycosylated suspensoside, a water soluble pheromone conjugate from the oral secretions of male Anastrepha suspensa Authors
Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 18, 2008
Publication Date: September 18, 2008
Citation: Walse, S.S., Lu, F., Teal, P.E. 2009. Glycosylated suspensoside, a water soluble pheromone conjugate from the oral secretions of male Anastrepha suspensa. Journal of Natural Products. 71(10):1726-1731. Interpretive Summary: Development of effective pheromone based attractants for Tephritid fly pests is important because the species are quarantine pests and pest outbreaks must be erradicated. Scientists at the Center for Medical, Agricultural and Veterinary Entomology-USDA-ARS have discovered that pheromone components including anastrephin, epianastrephin, produced by males of the Caribbean Fruit Fly, and other pest Tephritids in the genus Anastrepha, are deposited as '-hydroxy acid analogues linked to glucose at aggregation sites in oral secretions. When exposed to environmental conditions occurring when flies mate the '-hydroxy acid analogues are slowly released from the sugar water matrix in the form of the closed ring lactone pheromones anastrephin, epianastrephin and these attract both males and females to the mating sites. Use of these '-hydroxy acid glycosides in attractant lures will allow for slow release of defined ratios and amounts of pheromone components for the purposes of monitoring and control of Tephritid flies for which no effective pheromone based monitoring systems are available.
Technical Abstract: Oral secretions obtained from sexually mature males of the Caribbean fruit fly were attractive to both conspecific males and virgin females for more than 4 days. Collection of volatiles released over time from male oral secretions indicated that only anastrephin, epianastrephin were released from the secretions and that the rates of release of these two components were virtually constant over a 72h period. Chromatographic fractionation coupled with derivatization, enzymatic degradation, mass spectroscopy and nuclear magnetic resonance spectroscopy proved that both anastrephin and epianastrephin were bound to glucose by an '-1-glycosidic bond between glucose and the open ring form of the lactone pheromones. This is the first identification of a naturally produced slow release formulation for an insect pheromone and demonstrates that insect pheromones, linked to sugars via glycoside bonds, can be used as slow release formulations for dispensing synthetic pheromones for insect control.