| Title: | The pheromone production of female Plodia interpunctella is inhibited by tyraminergic antagonists |
| Author(s): | Hirashima A; Kimizu M; Shigeta Y; Matsugu S; Eiraku T; Kuwano E; Eto M; |
| Address: | "Department of Applied Genetics and Pest Management, Faculty of Agriculture, Graduate School, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan. ahirasim@agr.kyushu-u.ac.jp" |
| ISSN/ISBN: | 1612-1880 (Electronic) 1612-1872 (Linking) |
| Abstract: | "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-(14)C]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 common-featured models generated by the program Catalyst/HipHop, aromatic-ring (AR) and H-bond-acceptor-lipophilic (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" |
| Keywords: | "Animal Communication Animals Female Male Moths/*metabolism Octopamine/chemistry/metabolism/pharmacology Pheromones/*antagonists & inhibitors/*biosynthesis Protein Structure, Tertiary/physiology Sex Attractants/antagonists & inhibitors/biosynthesis Tyramin;" |
| Notes: | "MedlineHirashima, Akinori Kimizu, Megumi Shigeta, Yoko Matsugu, Sachiko Eiraku, Tomohiko Kuwano, Eiichi Eto, Morifusa eng Comparative Study Research Support, Non-U.S. Gov't Switzerland 2006/12/29 Chem Biodivers. 2004 Nov; 1(11):1652-67. doi: 10.1002/cbdv.200490124" |
