Degradation of an alkaloid pheromone from the pale-brown chafer, Phyllopertha diversa (Coleoptera: Scarabaeidae), by an insect olfactory cytochrome P450.
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.
Wojtasek
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Laboratory of Chemical Prospecting, National Institute of Sericultural and Entomological Science, Tsukuba, Japan.
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D000470:Alkaloids / Q000378:metabolism; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D001517:Coleoptera / Q000378:metabolism*; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D004791:Enzyme Inhibitors / Q000494:pharmacology; D019476:Insect Proteins / Q000378:metabolism*; D013058:Mass Spectrometry; D008797:Metyrapone / Q000494:pharmacology; D008861:Microsomes / Q000378:metabolism; D015394:Molecular Structure; D011335:Proadifen / Q000494:pharmacology; D011799:Quinazolines / Q000737:chemistry / Q000378:metabolism*; D012724:Sex Attractants / Q000378:metabolism*
D000470:Alkaloids; D065607:Cytochrome P-450 Enzyme Inhibitors; D004791:Enzyme Inhibitors; D019476:Insect Proteins; D011799:Quinazolines; D012724:Sex Attractants; C103499:1,3-dimethyl-2,4-(1H,3H)-quinazolinedione; D003577:Cytochrome P-450 Enzyme System; D011335:Proadifen; D008797:Metyrapone