Behavioral and electroantennogram responses of periplanone analogs

Abstract

The biological activities of synthetic periplanone analogs, including four candidates of periplanone-A (P-A), were evaluated by behavioral and electroantennogram (EAG) assays. Among 16 periplanone analogs, six compounds evoked pheromonal activity from the male American cockroaches. The threshold dosages of these biological active analogs were 10-10(5) times lower than that of the known periplanone mimic, germacrene-D. The conformation required for eliciting the pheromonal activity is discussed in terms of the structure-activity relationship of these analogs. Hauptmann's P-A elicited the strongest pheromonal activity among four candidates of P-A in our bioassay, suggesting that Hauptmann's P-A is a natural P-A produced from female cockroaches.

Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

“…Persoons et al (5) identified the first cockroach pheromone component from P. americana and named it periplanone-B. A second, structurally related compound, periplanone-A, was also identified from P. americana (6,7), whereas a similar structure (periplanone-J) has been proposed as the pheromone of P. japonica (8).…”

Behavioral and Electroantennogram Responses of Male American Cockroaches to Periplanones and Their Analogs

“…The behavioral assay was done essentially by the same procedure described by us before. 9 ) In this study, the threshold values were defined as the dosage at which significant locomotory activity was observed and more than half the number of the tested insects raised their wings. EAGs were recorded with glass capillary Ag-AgCl electrodes filled with TES Ringer.…”