β-Ionone as putative semiochemical suggested by ligand binding on an odorant-binding protein of Hylamorpha elegans and electroantennographic recordings

A - Papers appearing in refereed journals

Venthur, H., Zhou, J-J., Mutis, A., Ceballos, R., Mella-Herrera, R., Larama, G., Avila, A., Iturriaga-Vasquez, P., Faundez-Parragues, M., Alvear, M. and Quiroz, A. 2016. β-Ionone as putative semiochemical suggested by ligand binding on an odorant-binding protein of Hylamorpha elegans and electroantennographic recordings. Entomological Science. 19 (3), pp. 188-200.

AuthorsVenthur, H., Zhou, J-J., Mutis, A., Ceballos, R., Mella-Herrera, R., Larama, G., Avila, A., Iturriaga-Vasquez, P., Faundez-Parragues, M., Alvear, M. and Quiroz, A.
Abstract

Currently, odorant-binding proteins (OBPs) are considered the first filter for olfactory information for insects and constitute an interesting target for pest control. Thus, an OBP (HeleOBP) from the scarab beetle Hylamorpha elegans (Burmeister) was identified, and ligand-binding assays based on fluorescence and in silico approaches were performed, followed by a simulated binding assay. Fluorescence binding assays showed slight binding for most of the ligands tested, including host-plant volatiles. A high binding affinity was obtained for -ionone, a scarab beetle-related compound. However, the binding of its analogue -ionone was weaker, although it is still considered good. On the other hand, through a three-dimensional model of HeleOBP constructed by homology, molecular docking was carried out with 29 related ligands to the beetle. Results expressed as free binding energy and fit quality (FQ) indicated strong interactions of sesquiterpenes and terpenoids (- and -ionone) with HeleOBP as well as some aromatic compounds. Residues such as His102, Tyr105 and Tyr113 seemed to participate in the interactions previously mentioned. Both in silico scores supported the experimental affinity for the strongest ligands. Therefore, the activity of -ionone, -ionone and 2-phenyl acetaldehyde at antennal level was studied using electroantenography (EAG). Results showed that the three ligands are electrophysiologically active. However, an aliquot of -ionone (represented by 3.0ng) elicited stronger EAG responses in antennae of males than of females. Finally, the role of these ligands as potential semiochemicals for H.elegans is discussed.

KeywordsEntomology
Year of Publication2016
JournalEntomological Science
Journal citation19 (3), pp. 188-200
Digital Object Identifier (DOI)doi:10.1111/ens.12180
Open accessPublished as non-open access
FunderNLHPC at Centro de Modelacion y Computacion Cientifica, Universidad de La Frontera, CMCC-UFRO, Chile [ECM-02]
Rothamsted Research
Biotechnology and Biological Sciences Research Council
CONICYT
DIUFRO DI
Funder project or codeSustainability
Innovative approaches to pest management
UK-China Collaboration for production of biologically active homoisoprenoids and their eventual use for pest control
New pest resistance in rice, by breeding and genetic modification (GM) for constitutive and inducible levels of defence homoterpenes
PublisherWiley
Grant ID10-0018
21110933
ECM-02
ISSN1343-8786

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