Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis

• Published in: Journal of chemical ecology Vol. 33; no. 3; pp. 555 - 565
• Main Authors: Zarbin, Paulo H. G, Lorini, Lisete M, Ambrogi, Bianca G, Vidal, Diogo M, Lima, Eraldo R
• Format: Journal Article
• Language: English
• Published: New York, NY New York : Kluwer Academic Publishers-Plenum Publishers 01.03.2007; Springer; Springer Nature B.V
• Subjects: (E)-11-hexadecenol; (E)-11-Hexadecenyl acetate; age; Animal and plant ecology; Animal, plant and microbial ecology; Animals; Autoecology; Bioassays; Biological and medical sciences; Biological Assay; biosynthesis; calling behavior; chemical composition; Chromatography, Gas; diurnal variation; electroantennography; Female; female age; Females; Fundamental and applied biological sciences. Psychology; Insects; Lepidoptera; Lepidoptera - metabolism; Lepidoptera - physiology; Lithium; Lonomia obliqua; Magnetic Resonance Spectroscopy; Male; mating behavior; Medically important nuisances and vectors, pests of stored products and materials: population survey and control; Nuisances; olfactometry; Pest control; pheromone blends; pheromone calling; pheromone glands; Pheromones; Protozoa. Invertebrata; Retention time; Saturniidae; scotophase; Sex Attractants - biosynthesis; Sex Attractants - chemistry; sex pheromones; Sexual Behavior, Animal; synthetic pheromones; Mating call; Laboratory study; Sex pheromone; Nuisance; Insecta; Attacidae; Sexual behavior; Daily variation; Hemorrhagic caterpillar; Acetate; (E)-11-Hexadecenol· Calling behavior; Arthropoda; Lepidoptera; Chemical composition; Invertebrata; Chemical synthesis; Integrated pest management; (E)- 11 -Hexadecenyl acetate; Age; Semiochemicals
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-006-9246-1

The sex pheromone of Lonomia obliqua Walker (Lepidoptera: Saturniidae) was studied in the laboratory. All female calling occurred during the scotophase. Most females (70.6%) called first within 24 hr of eclosion. Calling varied with age of female, with older (5- to 6-day-old) females calling earlier in the scotophase and for longer durations than younger (0- to 1-day-old) females. The sex pheromone gland of 1- to 3-day-old virgin females was extracted during the calling peak. A Y-olfactometer bioassay showed significant attraction of males to a filter paper containing the female gland extract. Gas chromatographic-electroantennogram detection (GC-EAD) analysis of the extract indicated the presence of at least two possible pheromone components. Gas chromatographic-mass spectrometric analysis of the major GC-EAD-active peak indicated a hexadecenyl acetate; chemical derivatization indicated Δ11 unsaturation. Synthetic samples of (E)- and (Z)-11-hexadecenyl acetate were obtained by coupling 10-bromo-1-decanol and 1-hexyne, utilizing lithium chemistry. The comparison of the retention time of dimethyl disulfide derivatives of the natural compound, to those of synthetic chemicals, confirmed the natural compound as (E)-11-hexadecenyl acetate. The minor component was identified as the related alcohol, (E)-11-hexadecenol. The ratio of the two components in female extract was 100:35. Preliminary tests of males in a Y-olfactometer showed that their response to a mixture of the two compounds was not significantly different from that to gland extract.