Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach.
Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, 1c with a fluorine substituent instead of the chlorine and 1d with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that 1a and 1c are active, while 1b and 1d are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active.
Mori
K
K
Department of Chemistry, Faculty of Science, Science University of Tokyo, Japan.
Nakayama
T
T
Sakuma
M
M
D000818:Animals; D001522:Behavior, Animal; D001681:Biological Assay; D003058:Cockroaches / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012503:Saponins / Q000138:chemical synthesis*; D012724:Sex Attractants / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013265:Stigmasterol / Q000031:analogs & derivatives*
D012503:Saponins; D012724:Sex Attractants; C101368:blattellastanoside A; D013265:Stigmasterol