| Title: | Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae |
| Author(s): | Vidal DM; Moreira MAB; Coracini MDA; Zarbin PHG; |
| Address: | "Departamento de Quimica - Laboratorio de Semioquimicos, Universidade Federal do Parana, Curitiba, PR, Brazil. Departamento de Quimica, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil. Embrapa Tabuleiros Costeiros, Aracaju, SE, Brazil. Centro de Ciencias Biologicas e da Saude, Universidade Estadual do Oeste do Parana, Cascavel, PR, Brazil. Departamento de Quimica - Laboratorio de Semioquimicos, Universidade Federal do Parana, Curitiba, PR, Brazil. pzarbin@ufpr.br" |
| DOI: | 10.1038/s41598-018-37156-8 |
| ISSN/ISBN: | 2045-2322 (Electronic) 2045-2322 (Linking) |
| 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 (beta-Dex325(R)), 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" |
| Keywords: | "Animals Behavior, Animal Chromatography, Gas Cyclohexanones/chemistry/*isolation & purification Female Male Molecular Structure Pheromones/*chemistry/isolation & purification Sex Characteristics Weevils/metabolism/*physiology;" |
| Notes: | "MedlineVidal, Diogo Montes Moreira, Marcos Antonio Barbosa Coracini, Miryan Denise Araujo Zarbin, Paulo Henrique Gorgatti eng Research Support, Non-U.S. Gov't England 2019/01/30 Sci Rep. 2019 Jan 28; 9(1):776. doi: 10.1038/s41598-018-37156-8" |
