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Degradation of an alkaloid pheromone from the pale‐brown chafer, Phyllopertha diversa (Coleoptera: Scarabaeidae), by an insect olfactory cytochrome P450
Author(s) -
Wojtasek Hubert,
Leal Walter S
Publication year - 1999
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/s0014-5793(99)01178-3
Subject(s) - pheromone , biology , alkaloid , hydroxylation , scarabaeidae , biochemistry , sex pheromone , cytochrome p450 , stereochemistry , enzyme , botany , chemistry
The pale‐brown chafer, Phyllopertha diversa , utilizes an unusual alkaloid, 1,3‐dimethyl‐2,4‐(1 H ,3 H )‐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.