(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevil Conotrachelus psidii (Coleoptera: Curculionidae)

• Published in: Bioscience, biotechnology, and biochemistry Vol. 80; no. 5; pp. 848 - 855
• Main Authors: Romero-Frías, Alicia, Murata, Yasuhiro, Simões Bento, José Maurício, Osorio, Coralia
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.05.2016
• Subjects: 2,6-Dimethyl-3-oxabicyclo[4.2.0]octane-2-carbaldehyde; aggregation pheromone; Aldehydes - isolation & purification; Aldehydes - pharmacology; Animals; Behavior, Animal - drug effects; Behavior, Animal - physiology; Biological Assay; Bridged Bicyclo Compounds, Heterocyclic - isolation & purification; Bridged Bicyclo Compounds, Heterocyclic - pharmacology; Conotrachelus psidii; Female; Fruit - parasitology; Gas Chromatography-Mass Spectrometry; Male; Pheromones - isolation & purification; Pheromones - pharmacology; Psidium - parasitology; Solid Phase Microextraction; Volatile Organic Compounds - isolation & purification; Volatile Organic Compounds - pharmacology; Weevils - drug effects; Weevils - physiology; Y-tube olfactometer bioassay; aggregation pheromone; Conotrachelus psidii; 2,6-Dimethyl-3-oxabicyclo[4.2.0]octane-2-carbaldehyde; Y-tube olfactometer bioassay
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1080/09168451.2015.1136877

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. C. psidii male-specific volatiles collected by DHS and HS-SPME.