Title: | "Degradation of an alkaloid pheromone from the pale-brown chafer, Phyllopertha diversa (Coleoptera: Scarabaeidae), by an insect olfactory cytochrome P450" |
Address: | "Laboratory of Chemical Prospecting, National Institute of Sericultural and Entomological Science, Tsukuba, Japan" |
DOI: | 10.1016/s0014-5793(99)01178-3 |
ISSN/ISBN: | 0014-5793 (Print) 0014-5793 (Linking) |
Abstract: | "The pale-brown chafer, Phyllopertha diversa, utilizes an unusual alkaloid, 1,3-dimethyl-2,4-(1H,3H)-quinazolinedione, as its sex pheromone. This compound is rapidly degraded in vitro by the antennal protein extracts from this scarab beetle. Demethylation at the N-1 position and hydroxylation of the aromatic ring have been identified as the major catabolic pathways. The enzyme responsible for the pheromone degradation is membrane-bound, requires NAD(P)H for activity and is sensitive to cytochrome P450 inhibitors, such as proadifen and metyrapone. The ability to metabolize this unusual pheromone was not detected in 12 species tested, indicating that the P450 system, specific to male P. diversa antennae, has evolved as a mechanism for olfactory signal inactivation" |
Keywords: | "Alkaloids/metabolism Animals Chromatography, High Pressure Liquid Chromatography, Thin Layer Coleoptera/*metabolism Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Enzyme System/*metabolism Enzyme Inhibitors/pharmacology Insect Proteins/*metabolism Ma;" |
Notes: | "MedlineWojtasek, H Leal, W S eng Research Support, Non-U.S. Gov't England 1999/11/26 FEBS Lett. 1999 Sep 24; 458(3):333-6. doi: 10.1016/s0014-5793(99)01178-3" |