TY - JOUR
T1 - The pheromone production of female plodia interpunctella is inhibited by tyraminergic antagonists
AU - Hirashima, Akinori
AU - Kimizu, Megumi
AU - Shigeta, Yoko
AU - Matsugu, Sachiko
AU - Eiraku, Tomohiko
AU - Kuwano, Eiichi
AU - Eto, Morifusa
PY - 2004/11/1
Y1 - 2004/11/1
N2 - Several compounds were found to suppress the calling behavior and in vitro pheromone biosynthesis of the Indian meal moth, Plodia interpunctella. The compounds were screened by means of a calling-behavior bioassay with female P. interpunctella. Five derivatives with activities in the nanomolar range were identified, in order of decreasing pheromonostatic activity: 4-hydroxybenzaldehyde semicarbazone (42) >5-(4-methoxyphenyl)-1,3- oxazole (38) -5-[4-(tert-butyl)phenyl]-1,3-oxazole (40) >5-(3-methoxyphenyl)-1,3- oxazole (35) >5-(4- cyanophenyl)-1,3-oxazole (36). These compounds also showed in vitro inhibitory activity in intracellular de novo pheromone biosynthesis, as determined with isolated pheromone-gland preparations that incorporated [1-14C]sodium acetate in the presence of the so-called pheromone-biosynthesis-activating neuropeptide (PBAN). The non-additive effect of the inhibitor with antagonist (yohimbine) for the tyramine (TA) receptor suggests that it could be a tyraminergic antagonist. Three-dimensional (3D) computer models were built from a set of compounds. Among the commonfeatured models generated by the program Catalyst/HipHop, aromatic-ring (AR) and H-bond-acceptorlipophilic (HBAl) features were considered to be essential for inhibitory activity in the calling behavior and in vitro pheromone biosynthesis. Active compounds, including yohimbine, mapped well onto all the AR and HBAl features of the hypothesis. Less-active compounds were shown to be unable to achieve an energetically favorable conformation, consistent with our 3D common-feature pharmacophore models. The present hypothesis demonstrates that calling behavior and PBAN-stimulated incorporation of radioactivity are inhibited by tyraminergic antagonists.
AB - Several compounds were found to suppress the calling behavior and in vitro pheromone biosynthesis of the Indian meal moth, Plodia interpunctella. The compounds were screened by means of a calling-behavior bioassay with female P. interpunctella. Five derivatives with activities in the nanomolar range were identified, in order of decreasing pheromonostatic activity: 4-hydroxybenzaldehyde semicarbazone (42) >5-(4-methoxyphenyl)-1,3- oxazole (38) -5-[4-(tert-butyl)phenyl]-1,3-oxazole (40) >5-(3-methoxyphenyl)-1,3- oxazole (35) >5-(4- cyanophenyl)-1,3-oxazole (36). These compounds also showed in vitro inhibitory activity in intracellular de novo pheromone biosynthesis, as determined with isolated pheromone-gland preparations that incorporated [1-14C]sodium acetate in the presence of the so-called pheromone-biosynthesis-activating neuropeptide (PBAN). The non-additive effect of the inhibitor with antagonist (yohimbine) for the tyramine (TA) receptor suggests that it could be a tyraminergic antagonist. Three-dimensional (3D) computer models were built from a set of compounds. Among the commonfeatured models generated by the program Catalyst/HipHop, aromatic-ring (AR) and H-bond-acceptorlipophilic (HBAl) features were considered to be essential for inhibitory activity in the calling behavior and in vitro pheromone biosynthesis. Active compounds, including yohimbine, mapped well onto all the AR and HBAl features of the hypothesis. Less-active compounds were shown to be unable to achieve an energetically favorable conformation, consistent with our 3D common-feature pharmacophore models. The present hypothesis demonstrates that calling behavior and PBAN-stimulated incorporation of radioactivity are inhibited by tyraminergic antagonists.
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U2 - 10.1002/cbdv.200490124
DO - 10.1002/cbdv.200490124
M3 - Article
C2 - 17191806
AN - SCOPUS:35448948073
VL - 1
SP - 1652
EP - 1667
JO - Chemistry and Biodiversity
JF - Chemistry and Biodiversity
SN - 1612-1872
IS - 11
ER -