Degradation of an alkaloid pheromone from the pale‐brown chafer, <i>Phyllopertha diversa</i> (Coleoptera: Scarabaeidae), by an insect olfactory cytochrome P450

Wojtasek, Hubert; Leal, Walter S.

doi:10.1016/s0014-5793(99)01178-3

Cited by 72 publications

(42 citation statements)

References 27 publications

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“…PdivPDE is specific to antennae (see above). Pheromone degradation by antennal enzyme(s) is inhibited by metyrapone (12). Electrophysiological studies (2,3,(21)(22)(23)(24)(25) led to mapping the pheromone-detecting sensilla placodea and those tuned to other semiochemicals in P. diversa and other scarab beetle species.…”

Section: Resultsmentioning

confidence: 99%

“…1. Structures of P. diversa sex pheromone DMQ (1) and metyrapone, a compound that inhibits pheromone degradation by a male antennae-specific cytochrome P450 (12).…”

Section: Methodsmentioning

confidence: 99%

“…First, DMQ is specifically degraded by antennal extracts from P. diversa, and the enzymatic activity is due to cytochrome P450(s), which is inhibited in vitro by metyrapone (12). Second, P. diversa expresses at least one antennae-specific cytochrome P450 (this paper).…”

Section: Figmentioning

confidence: 96%

“…We have previously demonstrated that the antennal enzyme involved in pheromone degradation is membranebound, requires NAD(P)H, and is sensitive to cytochrome P450 inhibitors (12). Given that several attempts to isolate the enzyme were (not surprisingly) unrewarding, we took a bioinformatics approach to obtain the cDNAs encoding antennae-specific cytochrome P450s.…”

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confidence: 99%

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Pheromone anosmia in a scarab beetle induced by in vivo inhibition of a pheromone-degrading enzyme

Maı̈bèche-Coisné

Nikonov

Ishida

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

118

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Previous biochemical evidence suggests that a cytochrome P450 specific to male antennae of the pale-brown chafer, Phyllopertha diversa, has evolved as a pheromone-degrading enzyme. By using a bioinformatics approach, we have now cloned three P450 cDNAs: CYP4AW1, CYP4AW2, and CYP6AT1. RT-PCR indicated that CYP4AW2 is expressed in all tissues examined, that CYP6AT1 is antennae-rich, and that CYP4AW1 is antennae-specific. Both tissue specificity and electrophysiological studies strongly support that CYP4AW1 in P. diversa is a pheromone-degrading enzyme involved in pheromone inactivation. Highly sensitive, pheromone-specific olfactory receptor neurons in male antennae were completely desensitized by direct application of metyrapone into the sensillar lymph. When tested in the same or different individuals, the metyrapone treatment had no effect on olfactory receptor neurons tuned to the plant volatile (Z)-3-hexenyl acetate, which might be inactivated by an esterase. Metyrapone treatment did not affect pheromone reception in the Japanese beetle, Popillia japonica, in the scarab beetle, Anomala octiescostata, or in the Oriental beetle, Exomala orientalis. Metyrapone-induced anosmia was restricted to the pheromone detectors in P. diversa, which became insensitive to physiological concentrations of pheromones for a few minutes. As opposed to previous trials, the specificity of the inhibitor and pheromone system led to unambiguous evidence for the role of pheromone-degrading enzymes in the fast inactivation of pheromones. Insects rely heavily on their chemical communication skills to perform fundamental behaviors. Females, for example, advertise their readiness to mate and recruit males for reproduction by releasing sex pheromones. To avoid ''chemical conspicuousness,'' they release minute amounts of the species-specific chemical signals. To detect low levels of such unique signals in a noisy environment, males have evolved sensory systems with remarkable sensitivity that are highly tuned to these species-specific pheromones. Females of the pale-brown chaffer Phyllopertha diversa (Coleoptera or Scarabaeidae), for example, produce an alkaloid pheromone, 1,3-dimethyl-2,4-(1H,3H)-quinazolinedione (DMQ) (Fig. 1) (1), which is specifically detected by highly sensitive olfactory receptor neurons in male antennae (2, 3).While taking an odorant-oriented flight toward a pheromoneemitting female, a male encounters intermittent chemical signals comprising short bursts of high flux separated by periods during which the flux is zero (4, 5). Sustainable flight and orientation requires that the sensory system be reset on a millisecond timescale while navigating through the ''clean'' space between filaments. Two dichotomous hypotheses have been suggested for the fast inactivation of chemical signals. Based on the estimation that in the presence of an antennae-specific pheromonedegrading enzyme (PDE) (6) the pheromone has a half-life of 15 ms, it has been suggested that pheromone signals are deactivated by an enzymatic process (7). On th...

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Section: Resultsmentioning

confidence: 99%

“…1. Structures of P. diversa sex pheromone DMQ (1) and metyrapone, a compound that inhibits pheromone degradation by a male antennae-specific cytochrome P450 (12).…”

Section: Methodsmentioning

confidence: 99%

Section: Figmentioning

confidence: 96%

mentioning

confidence: 99%

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Pheromone anosmia in a scarab beetle induced by in vivo inhibition of a pheromone-degrading enzyme

Maı̈bèche-Coisné

Nikonov

Ishida

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

118

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“…Studies on the degradation along with potential cofactors or inhibitors showed that the enzymatic system requires NADPH and NADH for activity. On the other hand, the enzymatic activity was inhibited by proadifen and metyrapone, two general widely used inhibitors for cytochrome P450 [11].…”

Section: Pheromone-degrading Enzymesmentioning

confidence: 99%

Molecules and macromolecules involved in chemical communication of scarab beetles

Leal

2001

Pure and Applied Chemistry

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Chemical communication involves the production and release of specific chemicals (pheromones and other semiochemicals) by the emitter, and the detection and olfactory processing of these signals leading to appropriate behavioral responses in the receiver. In contrast to most of the scarab species investigated to date, the Japanese and Osaka beetles have the ability to detect the allospecific pheromone, which plays a pivotal role in the isolation mechanism between these two species. Each species produces a single enantiomer of japonilure [(Z)-5-(dec1-enyl)oxacyclopentan-2-one], but they have evolved the ability to detect both enantiomers, one as an attractant and the other as a behavioral antagonist (stop signal). There is growing evidence in the literature that the inordinate sensitivity and selectivity of the insect olfactory system is achieved by a combination of various olfactory-specific proteins, namely, odorant-binding proteins (OBPs), odorant receptors (ORs), and odorant-degrading enzymes. The relationship between the pheromone structures and the primary sequences of the proteins suggest that OBPs play a part in the selectivity of the olfactory system in scarab beetles by "filtering" chemical signals during the early olfactory processing (perireceptor events). Nevertheless, it is unlikely that pheromone-binding proteins are "chiral filters" as the Japanese and Osaka beetles each possess only one single binding protein. Upon interaction with negatively charged membranes, OBPs undergo conformational changes that may lead to the release of the ligands. PHEROMONE CHEMISTRYRecent studies have led to the identification of the sex pheromones of various species in the subfamily Rutelinae and Melolonthinae [1]. In general, the pheromones of the former are fatty acid-derived compounds [2], whereas the latter utilizes phenolic, terpenoid, and amino acid-derived compounds. Two interesting exceptions to this general rule are the pheromones of Heptophylla picea and Phyllopertha diversa. Although belonging to the Melolonthinae, H. picea utilizes (R,Z)-7,15-hexadecadien-4-olide [3], most likely biosynthesized from stearic acid. On the other hand, P. diversa (Rutelinae) produces an intriguing alkaloid pheromone, which also has medicinal properties [4].Utilizing pheromone blends that consist of just a few semiochemicals or even a single constituent, closely related species have attained isolated chemical communication channels and reproductive isolation [5,6]. Species that have the same pheromone system are isolated either temporarily or geographically. Interestingly, Anomala osakana and Popillia japonica utilize enantiomers of a chiral pheromone (japonilure), with one stereoisomer being an attractant and the other a behavioral antagonist. P. japonica and A. osakana produce (R)-and (S)-japonilure, respectively [7,8]. The pheromone of one species is a behavioral antagonist for the other. It seems that this agonist-anatagonist activities of the enantiomeric pheromones have evolved as part of the isolation mechanism...

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Has gene expression neofunctionalization in the fire ant antennae contributed to queen discrimination behavior?

Dang

Cohanim

Fontana

et al. 2019

Ecology and Evolution

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Queen discrimination behavior in the fire ant Solenopsis invicta maintains its two types of societies: colonies with one (monogyne) or many (polygyne) queens, yet the underlying genetic mechanism is poorly understood. This behavior is controlled by two supergene alleles, SB and Sb, with ~600 genes. Polygyne workers, having either the SB/SB or SB/Sb genotype, accept additional SB/Sb queens into their colonies but kill SB/SB queens. In contrast, monogyne workers, all SB/SB, reject all additional queens regardless of genotype. Because the SB and Sb alleles have suppressed recombination, determining which genes within the supergene mediate this differential worker behavior is difficult. We hypothesized that the alternate worker genotypes sense queens differently because of the evolution of differential expression of key genes in their main sensory organ, the antennae. To identify such genes, we sequenced RNA from four replicates of pooled antennae from three classes of workers: monogyne SB/SB, polygyne SB/SB, and polygyne SB/Sb. We identified 81 differentially expressed protein‐coding genes with 13 encoding potential chemical metabolism or perception proteins. We focused on the two odorant perception genes: an odorant receptor SiOR463 and an odorant‐binding protein SiOBP12. We found that SiOR463 has been lost in the Sb genome. In contrast, SiOBP12 has an Sb‐specific duplication, SiOBP12b′, which is expressed in the SB/Sb worker antennae, while both paralogs are expressed in the body. Comparisons with another fire ant species revealed that SiOBP12b′ antennal expression is specific to S. invicta and suggests that queen discrimination may have evolved, in part, through expression neofunctionalization.

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Degradation of an alkaloid pheromone from the pale‐brown chafer, Phyllopertha diversa (Coleoptera: Scarabaeidae), by an insect olfactory cytochrome P450

Cited by 72 publications

References 27 publications

Pheromone anosmia in a scarab beetle induced by in vivo inhibition of a pheromone-degrading enzyme

Pheromone anosmia in a scarab beetle induced by in vivo inhibition of a pheromone-degrading enzyme

Molecules and macromolecules involved in chemical communication of scarab beetles

Has gene expression neofunctionalization in the fire ant antennae contributed to queen discrimination behavior?

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