| Title: | Identification of male-produced aggregation pheromone of the curculionid beetle Sternechus subsignatus |
| Author(s): | Ambrogi BG; Cortes AM; Zarbin PH; |
| Address: | "Laboratorio de Semioquimicos, Departamento de Quimica, Universidade Federal do Parana, CP 19081, CEP 81531-990, Curitiba, PR, Brazil" |
| DOI: | 10.1007/s10886-012-0080-3 |
| ISSN/ISBN: | 1573-1561 (Electronic) 0098-0331 (Linking) |
| Abstract: | "Analyses of the headspace volatiles produced by males and females of Sternechus subsignatus Boheman (Coleoptera: Curculionidae) revealed seven male-specific compounds. The major component was (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, and the minor components were 1-(2'-hydroxyethyl)-1-methyl-2-isopropenylcyclobutane (grandisol), 7-methyl-3-methyleneoct-6-en-1-ol, (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol, (Z)- and (E)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, and (E)-2-(3,3-dimethylcyclohexylidene) acetic acid. The latter compound is described for the first time as a natural product. Only four of the seven identified compounds showed electrophysiological activity. Enantioselective gas chromatography showed that the natural grandisol is the (1R,2S)-stereoisomer. The major component, (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, attracted S. subsignatus in olfactometer bioassays. Studies are in progress to evaluate the biological activity of the major component and the EAD-active mixture under field conditions" |
| Keywords: | "Acetaldehyde/chemistry/metabolism Acetic Acid/chemistry/metabolism Animals Chromatography, Gas Ethanol/chemistry/metabolism Female Male Pheromones/*chemistry/*metabolism Stereoisomerism Terpenes/chemistry/metabolism Weevils/chemistry/*metabolism;" |
| Notes: | "MedlineAmbrogi, Bianca G Cortes, Angela M Palacio Zarbin, Paulo H G eng Research Support, Non-U.S. Gov't 2012/03/03 J Chem Ecol. 2012 Mar; 38(3):272-7. doi: 10.1007/s10886-012-0080-3. Epub 2012 Mar 1" |
