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J Chem Ecol

Title:		"Behavioral activity of stereoisomers and a new component of the contact sex pheromone of female German cockroach, Blattella germanica"
Author(s):		Eliyahu D; Mori K; Takikawa H; Leal WS; Schal C;
Address:		"Department of Entomology and W. M. Keck Center for Behavioral Biology, North Carolina State University, Raleigh, North Carolina 27695-7613, USA"
Journal Title:		J Chem Ecol
Year:		2004
Volume:		30
Issue:		9
Page Number:		1839 - 1848
DOI:		10.1023/b:joec.0000042405.05895.3a
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"(3S,11S)-3,11-Dimethylnonacosan-2-one is a major component of the courtship stimulating, contact sex pheromone of the female German cockroach. Although the four synthetic stereoisomers of this compound have been tested in behavioral assays, their relative activity remains unresolved. Using isolated male antennae dosed with synthetic test compounds to assay male behavior, we found that at high doses all four stereoisomers elicited responses from 100% of the males. However, at physiologically relevant doses similar to those found on the female antenna, the (3S,11S)-isomer was the least effective of the four stereoisomers at eliciting courtship responses in males. This is the first example of a natural stereoisomer having less bioactivity than related stereoisomers that do not occur naturally. Another component of the sex pheromone blend, 3,11-dimethylheptacosan-2-one, was previously purified from the female's epicuticule and behaviorally assayed, but its activity was not confirmed through synthesis. We now confirm that synthetic (3S,11S)-3,11-dimethylheptacosan-2-one elicits behavioral responses, but less so than its C29 homolog"
Keywords:		"Alkanes/chemistry/*pharmacology Animals Cockroaches/*drug effects/physiology Dose-Response Relationship, Drug Female Ketones/chemistry/*pharmacology Male Sense Organs/physiology Sex Attractants/chemistry/*pharmacology Stereoisomerism;"
Notes:		"MedlineEliyahu, Dorit Mori, Kenji Takikawa, Hirosato Leal, Walter S Schal, Coby eng Comparative Study Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2004/12/14 J Chem Ecol. 2004 Sep; 30(9):1839-48. doi: 10.1023/b:joec.0000042405.05895.3a"