Zingiberenol, (1S,4R,1′S)‑4-(1′,5′-Dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol, Identified as the Sex Pheromone Produced by Males of the Rice Stink Bug Oebalus poecilus (Heteroptera: Pentatomidae)

Bioassays using an olfactometer showed that Oebalus poecilus males produce the sexual pheromone, and the chemical analysis demonstrated that this compound is zingiberenol. Two groups of isomers, each containing four diastereoisomers, (1RS,4RS,1′S)- and (1RS,4RS,1′R)-zingiberenol, were prepared. Thes...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2013-08, Vol.61 (32), p.7777-7785
Main Authors: de Oliveira, Márcio Wandré Morais, Borges, Miguel, Andrade, Carlos Kleber Zago, Laumann, Raul Alberto, Barrigossi, José Alexandre Freitas, Blassioli-Moraes, Maria Carolina
Format: Article
Language:English
Subjects:
Animals
bioassays
carbon
chemical analysis
diastereomers
Female
females
ginger
Heteroptera - chemistry
Heteroptera - metabolism
Isomerism
Male
males
Molecular Structure
nuclear magnetic resonance spectroscopy
Oebalus poecilus
Oebalus pugnax
Oryza - parasitology
Plant Diseases - parasitology
Sesquiterpenes - chemistry
Sesquiterpenes - metabolism
Sex Attractants - chemistry
Sex Attractants - metabolism
sex pheromones
stereochemistry
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Summary:Bioassays using an olfactometer showed that Oebalus poecilus males produce the sexual pheromone, and the chemical analysis demonstrated that this compound is zingiberenol. Two groups of isomers, each containing four diastereoisomers, (1RS,4RS,1′S)- and (1RS,4RS,1′R)-zingiberenol, were prepared. These diastereoisomers were not separated on a chiral GC column. Therefore, to determine the absolute configuration of the carbon 1, 4, and 1′ of zingiberenol produced by males, the following strategies were conducted. The extract containing males volatiles was submitted to dehydration microchemistry to produce zingiberene, in which the isomers are separated by chiral GC analysis, and by comparison with the natural zingiberene from ginger oil, the absolute stereochemistry of the carbons 4 and 1′ was determined to be R and S, respectively, and the carbon 1 was determined as R from the 13C NMR spectra of quercivorol. Finally, the bioassays showed that O. poecilus females responded to racemic mixture and to (1RS,4RS,1′S)-zingiberenol.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf402765b