AGGREGATION ARRESTANT PHEROMONE OF THE GERMAN-COCKROACH, BLATTELLA-GERMANICA (L) (DICTYOPTERA, BLATTELLIDAE) - ISOLATION AND STRUCTURE ELUCIDATION OF BLATTELLASTANOSIDE-A AND BLATTELLASTANOSIDE-B

The aggregation pheromone of the German cockroach, Blattella germanica, consists of attractant and arrestant, which can be detected by olfactometer and choice-chamber assay, respectively. Both were extracted from the frass-contaminated filter paper being used as a shelter. They were separated by solvent partition with n-butanol and water. The arrestant from the n-butanol phase was purified by open column chromatography and then successive HPLC isolated two major arrestant components. Spectral evidence from SI-MS, HR-EI-MS, and NMR experiments with pulse techniques provided possible structures as 1-(6alpha-chloro-4beta,5beta-epoxy-50-stigmast-3beta-yl)-beta-D-glucopyranoside and 1-(6alpha-chloro-5beta-hydroxy-5beta-stigmast-3beta-yl)-beta-D-glucopyranoside, denoted as blattellastanoside-A and blattellastanoside-B, respectively. They represented arrestant activity as median effective doses (ED50) at 0.044 (A) and 3.2 (B) nmol on 1.0 cm2 of Whatman No. 1 filter paper.