New mimics of the acetate function in pheromone-based attraction.
Bioorg Med Chem
; 4(3): 479-88, 1996 Mar.
Article
en En
| MEDLINE
| ID: mdl-8733630
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.
Buscar en Google
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Atractivos Sexuales
/
Ácidos Grasos Monoinsaturados
/
Mariposas Nocturnas
Límite:
Animals
Idioma:
En
Revista:
Bioorg Med Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
1996
Tipo del documento:
Article
País de afiliación:
República Checa
Pais de publicación:
Reino Unido