Abstract |
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 (13)C NMR spectra of quercivorol. Finally, the bioassays showed that O. poecilus females responded to racemic mixture and to (1RS,4RS,1'S)-zingiberenol.
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Authors | Márcio Wandré Morais de Oliveira, Miguel Borges, Carlos Kleber Zago Andrade, Raul Alberto Laumann, José Alexandre Freitas Barrigossi, Maria Carolina Blassioli-Moraes |
Journal | Journal of agricultural and food chemistry
(J Agric Food Chem)
Vol. 61
Issue 32
Pg. 7777-85
(Aug 14 2013)
ISSN: 1520-5118 [Electronic] United States |
PMID | 23879882
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- (1RS,4RS,1'S)-zingiberenol
- Sesquiterpenes
- Sex Attractants
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Topics |
- Animals
- Female
- Heteroptera
(chemistry, metabolism)
- Isomerism
- Male
- Molecular Structure
- Oryza
(parasitology)
- Plant Diseases
(parasitology)
- Sesquiterpenes
(chemistry, metabolism)
- Sex Attractants
(chemistry, metabolism)
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