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New mimics of the acetate function in pheromone-based attraction.

Abstract：

: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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Hoskovec M,Hovorka O,Kalinová B,Koutek B,Streinz L,Svatos A,Sebek P,Saman D,Vrkoc J

doi

10.1016/0968-0896(96)00029-6

subject

Has Abstract

pub_date

1996-03-01 00:00:00

pages

479-88

issue

3

eissn

0968-0896

issn

1464-3391

pii

0968-0896(96)00029-6

journal_volume

4

pub_type

杂志文章

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