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Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae

The beetle Homalinotus depressus (Coleoptera: Curculionidae) is a major pest of coconuts in the Northern region of Brazil, for which environmentally friendly methods of control are desired. Behavioral responses of H. depressus to airborne volatile extracts from conspecifics suggested the presence of...

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Autores principales: Vidal, Diogo Montes, Moreira, Marcos Antonio Barbosa, Coracini, Miryan Denise Araujo, Zarbin, Paulo Henrique Gorgatti
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
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Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349938/
https://www.ncbi.nlm.nih.gov/pubmed/30692570
http://dx.doi.org/10.1038/s41598-018-37156-8
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author Vidal, Diogo Montes
Moreira, Marcos Antonio Barbosa
Coracini, Miryan Denise Araujo
Zarbin, Paulo Henrique Gorgatti
author_facet Vidal, Diogo Montes
Moreira, Marcos Antonio Barbosa
Coracini, Miryan Denise Araujo
Zarbin, Paulo Henrique Gorgatti
author_sort Vidal, Diogo Montes
collection PubMed
description The beetle Homalinotus depressus (Coleoptera: Curculionidae) is a major pest of coconuts in the Northern region of Brazil, for which environmentally friendly methods of control are desired. Behavioral responses of H. depressus to airborne volatile extracts from conspecifics suggested the presence of a male-produced aggregation pheromone. GC analyses of these extracts showed the presence of four male-specific compounds. Analytical data in combination with the synthesis of standards led to the identification of the male-released semiochemicals as epoxyisophorone (1), isophorone (2), homalinol (3), and 2-hydroxyisophorone (4), of which (3) was the major constituent. The configuration of homalinol was determined to be cis on the basis of retention times of synthetic cis and trans synthetic standards. Enantiomers of cis-homalinol were obtained in high enantiomeric excess by using biocatalysis. Their separation on a GC enantioselective column (β-Dex325®), allowed us to unambiguously determine that the absolute configuration of natural homalinol was (1R,2R,6S). Field bioassays demonstrated that both the synthetic major compound per se and mixtures of all four male-specific compounds were attractive to H. depressus.
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spelling pubmed-63499382019-01-30 Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae Vidal, Diogo Montes Moreira, Marcos Antonio Barbosa Coracini, Miryan Denise Araujo Zarbin, Paulo Henrique Gorgatti Sci Rep Article The beetle Homalinotus depressus (Coleoptera: Curculionidae) is a major pest of coconuts in the Northern region of Brazil, for which environmentally friendly methods of control are desired. Behavioral responses of H. depressus to airborne volatile extracts from conspecifics suggested the presence of a male-produced aggregation pheromone. GC analyses of these extracts showed the presence of four male-specific compounds. Analytical data in combination with the synthesis of standards led to the identification of the male-released semiochemicals as epoxyisophorone (1), isophorone (2), homalinol (3), and 2-hydroxyisophorone (4), of which (3) was the major constituent. The configuration of homalinol was determined to be cis on the basis of retention times of synthetic cis and trans synthetic standards. Enantiomers of cis-homalinol were obtained in high enantiomeric excess by using biocatalysis. Their separation on a GC enantioselective column (β-Dex325®), allowed us to unambiguously determine that the absolute configuration of natural homalinol was (1R,2R,6S). Field bioassays demonstrated that both the synthetic major compound per se and mixtures of all four male-specific compounds were attractive to H. depressus. Nature Publishing Group UK 2019-01-28 /pmc/articles/PMC6349938/ /pubmed/30692570 http://dx.doi.org/10.1038/s41598-018-37156-8 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Vidal, Diogo Montes
Moreira, Marcos Antonio Barbosa
Coracini, Miryan Denise Araujo
Zarbin, Paulo Henrique Gorgatti
Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
title Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
title_full Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
title_fullStr Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
title_full_unstemmed Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
title_short Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
title_sort isophorone derivatives as a new structural motif of aggregation pheromones in curculionidae
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349938/
https://www.ncbi.nlm.nih.gov/pubmed/30692570
http://dx.doi.org/10.1038/s41598-018-37156-8
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