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

Abstract 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 pr...

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Autores principales:	Diogo Montes Vidal, Marcos Antonio Barbosa Moreira, Miryan Denise Araujo Coracini, Paulo Henrique Gorgatti Zarbin
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2019
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/fdcd22bff5404be49b33c714530297b4
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spelling	oai:doaj.org-article:fdcd22bff5404be49b33c714530297b42021-12-02T15:09:49ZIsophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae10.1038/s41598-018-37156-82045-2322https://doaj.org/article/fdcd22bff5404be49b33c714530297b42019-01-01T00:00:00Zhttps://doi.org/10.1038/s41598-018-37156-8https://doaj.org/toc/2045-2322Abstract 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.Diogo Montes VidalMarcos Antonio Barbosa MoreiraMiryan Denise Araujo CoraciniPaulo Henrique Gorgatti ZarbinNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 9, Iss 1, Pp 1-12 (2019)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Diogo Montes Vidal Marcos Antonio Barbosa Moreira Miryan Denise Araujo Coracini Paulo Henrique Gorgatti Zarbin Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
description	Abstract 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.
format	article
author	Diogo Montes Vidal Marcos Antonio Barbosa Moreira Miryan Denise Araujo Coracini Paulo Henrique Gorgatti Zarbin
author_facet	Diogo Montes Vidal Marcos Antonio Barbosa Moreira Miryan Denise Araujo Coracini Paulo Henrique Gorgatti Zarbin
author_sort	Diogo Montes Vidal
title	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_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_sort	isophorone derivatives as a new structural motif of aggregation pheromones in curculionidae
publisher	Nature Portfolio
publishDate	2019
url	https://doaj.org/article/fdcd22bff5404be49b33c714530297b4
work_keys_str_mv	AT diogomontesvidal isophoronederivativesasanewstructuralmotifofaggregationpheromonesincurculionidae AT marcosantoniobarbosamoreira isophoronederivativesasanewstructuralmotifofaggregationpheromonesincurculionidae AT miryandenisearaujocoracini isophoronederivativesasanewstructuralmotifofaggregationpheromonesincurculionidae AT paulohenriquegorgattizarbin isophoronederivativesasanewstructuralmotifofaggregationpheromonesincurculionidae
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Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae

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