Sex pheromone of Lonomia obliqua: daily rhythm of production, identification, and synthesis.
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 delta11 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.
Zarbin
Paulo H G
PH
Departamento de Quimica, Laboratório de Semioquímicos, Universidade Federal do Paraná C. Postal 19081, 81531-990 Curitiba-PR, Brazil. pzarbin@quimica.ufpr.br
Lorini
Lisete M
LM
Ambrogi
Bianca G
BG
Vidal
Diogo M
DM
Lima
Eraldo R
ER
D000818:Animals; D001681:Biological Assay; D002849:Chromatography, Gas; D005260:Female; D007915:Lepidoptera / Q000378:metabolism* / Q000502:physiology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D012724:Sex Attractants / Q000096:biosynthesis* / Q000737:chemistry; D012726:Sexual Behavior, Animal
D012724:Sex Attractants