New mimics of the acetate function in pheromone-based attraction.
Several analogues of (Z)-8-dodecenyl acetate (1a), the major pheromone component of the Oriental fruit moth, Cydia molesta, with chloroformate and lactone functional groups in place of the acetate moiety, were synthesized and investigated for their biological activity at four evaluation levels, i.e. by electroantennography (EAG), electrosensillography (ESG), short-range sexual stimulation and activation in the flight-tunnel. We found very strict requirements on the shape as well as on the electron distribution of the acetate group for a productive interaction with the receptor. The behavioral results showed that, among the analogues investigated, the chloroformate 1b, alken-4-olide 2a and also dodecyl acetate (1c) possess significant (60-85%) inhibitory activities. Based on electrophysiological evidence demonstrating that (i) only 1b is competing with the major pheromone component 1a for the same receptor sites on the male antennal sensilla, (ii) 1c elicits moderate EAG but no ESG responses and (iii) 2a does not produce any electrophysiological response at all, three possible inhibitory mechanisms by which these analogues are acting could be distinguished.
Hoskovec
M
M
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
Hovorka
O
O
Kalinová
B
B
Koutek
B
B
Streinz
L
L
Svatos
A
A
Sebek
P
P
Saman
D
D
Vrkoc
J
J
D000818:Animals; D004305:Dose-Response Relationship, Drug; D004594:Electrophysiology; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D008297:Male; D018716:Molecular Mimicry; D009036:Moths / Q000502:physiology*; D012724:Sex Attractants / Q000737:chemistry*; D012726:Sexual Behavior, Animal; D013329:Structure-Activity Relationship
D005229:Fatty Acids, Monounsaturated; D012724:Sex Attractants; C026162:8-dodecenyl acetate