title: (1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevil Conotrachelus psidii (Coleoptera: Curculionidae).
abstract: The guava weevil, Conotrachelus psidii is an aggressive pest of guava (Psidium guajava L.) that causes irreparable damages inside the fruit. The volatile compounds of male and female insects were separately collected by headspace solid-phase microextraction or with dynamic headspace collection on a polymer sorbent, and comparatively analyzed by GC-MS. (1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane (papayanol), and (1R,2S,6R)-2,6-dimethyl-3-oxabicyclo[4.2.0]octane-2-carbaldehyde (papayanal) were identified (ratio of 9:1, respectively) as male-specific guava weevil volatiles. Papayanal structure was confirmed by comparison of spectroscopic (EIMS) and chromatographic (retention time) data with those of the synthetic pure compound. The behavioral response of the above-mentioned compounds was studied in a Y-tube olfactometer bioassay, and their role as aggregation pheromone candidate components was suggested in this species.
authors.affiliation: a Departamento de Química , Universidad Nacional de Colombia , Bogotá , Colombia.
authors.forename: Alicia
authors.initials: A
authors.lastname: Romero-Frías
authors.affiliation: b Fuji Flavor Co., Ltd. , Tokyo , Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Murata
authors.affiliation: c Departamento de Entomologia , Escola Superior de Agricultura Luiz de Queiroz (ESALQ), Universidade de São Paulo (USP) , Piracicaba , Brazil.
authors.forename: José Maurício
authors.initials: JM
authors.lastname: Simões Bento
authors.affiliation: a Departamento de Química , Universidad Nacional de Colombia , Bogotá , Colombia.
authors.forename: Coralia
authors.initials: C
authors.lastname: Osorio
mesh_terms: D000447:Aldehydes / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects / Q000502:physiology; D001681:Biological Assay; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000302:isolation & purification* / Q000494:pharmacology; D005260:Female; D005638:Fruit / Q000469:parasitology; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D010675:Pheromones / Q000302:isolation & purification* / Q000494:pharmacology; D031647:Psidium / Q000469:parasitology*; D052617:Solid Phase Microextraction; D055549:Volatile Organic Compounds / Q000302:isolation & purification* / Q000494:pharmacology; D048889:Weevils / Q000187:drug effects* / Q000502:physiology
chemical_list: C551343:(1R,2S,6R)-2-hydroxymethyl-2,6-dimethyl-3-oxabicyclo(4.2.0)octane; D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D010675:Pheromones; D055549:Volatile Organic Compounds
keywords: 2,6-Dimethyl-3-oxabicyclo[4.2.0]octane-2-carbaldehyde; Conotrachelus psidii; Y-tube olfactometer bioassay; aggregation pheromone