Essential amino acid methyl esters: major sex pheromone components of the cranberry white grub, Phyllophaga anxia (Coleoptera: Scarabaeidae)

Chiral capillary gas chromatographic-electroantennographic detection (GC-EAD) analysis indicates that L-valine and L-isoleucine methyl esters are the major sex pheromone components released by females of the cranberry white grub, Phyllophaga anxia (LeConte). The GC retention times and GC-mass spectr...

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Bibliographic Details
Published in:Journal of chemical ecology 1997-01, Vol.23 (1), p.231-245
Main Authors: Zhang, A, Robbins, P.S, Leal, W.S, Linn, C.E. Jr, Villani, M.G, Roelofs, W.L
Format: Article
Language:English
Subjects:
Animal and plant ecology
Animal, plant and microbial ecology
Animals
Autoecology
Biological and medical sciences
CHEMICAL COMPOSITION
Coleoptera
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
FEROMONAS SEXUALES
Fundamental and applied biological sciences. Psychology
PHEROMONE SEXUELLE
PHYLLOPHAGA ANXIA
Protozoa. Invertebrata
Scarabaeidae
SEX PHEROMONES
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Summary:Chiral capillary gas chromatographic-electroantennographic detection (GC-EAD) analysis indicates that L-valine and L-isoleucine methyl esters are the major sex pheromone components released by females of the cranberry white grub, Phyllophaga anxia (LeConte). The GC retention times and GC-mass spectrometry of the two natural compounds were identical to those of authentic standards. Of five reproducible GC-EAD active components revealed with female volatiles, the L-valine and L-isoleucine methyl esters elicited the strongest male antennal responses. The ratio of L-valine and L-isoleucine methyl esters was determined to be 3:1 by analysis of pheromone gland extracts. Chirality was shown to be critical by GC-EAD, since only the L-form of these amino acid methyl esters elicited an EAD response. In field experiments conducted in Massachusetts, a synthetic 3:1 blend of L-valine and L-isoleucine methyl esters on a rubber septum was attractive to P. anxia males
ISSN:0098-0331
1573-1561
DOI:10.1023/B:JOEC.0000006356.47959.ed