« Previous Abstract"Pharmaceuticals residues and xenobiotics contaminants: Occurrence, analytical techniques and sustainable alternatives for wastewater treatment"    Next AbstractSilicon-induced changes in plant volatiles reduce attractiveness of wheat to the bird cherry-oat aphid Rhopalosiphum padi and attract the parasitoid Lysiphlebus testaceipes »

J Agric Food Chem

Title:		"Zingiberenol, (1R,4R,1'S)?ª╡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)"
Author(s):		de Oliveira MW; Borges M; Andrade CK; Laumann RA; Barrigossi JA; Blassioli-Moraes MC;
Address:		"Embrapa Recursos Geneticos e Biotecnologia , Parque Estacao Biologica - W5 Norte, CEP 70770-900, Brasilia, DF, Brazil"
Journal Title:		J Agric Food Chem
Year:		2013
Volume:		20130806
Issue:		32
Page Number:		7777 - 7785
DOI:		10.1021/jf402765b
ISSN/ISBN:		1520-5118 (Electronic) 0021-8561 (Linking)
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"
Keywords:		Animals Female Heteroptera/chemistry/*metabolism Isomerism Male Molecular Structure Oryza/*parasitology Plant Diseases/parasitology Sesquiterpenes/chemistry/*metabolism Sex Attractants/chemistry/*metabolism;
Notes:		"Medlinede Oliveira, Marcio Wandre Morais Borges, Miguel Andrade, Carlos Kleber Zago Laumann, Raul Alberto Barrigossi, Jose Alexandre Freitas Blassioli-Moraes, Maria Carolina eng Research Support, Non-U.S. Gov't 2013/07/25 J Agric Food Chem. 2013 Aug 14; 61(32):7777-85. doi: 10.1021/jf402765b. Epub 2013 Aug 6"