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J Chem Ecol

Title:		Identification and synthesis of a male-produced pheromone for the neotropical root weevil Diaprepes abbreviatus
Author(s):		Lapointe SL; Alessandro RT; Robbins PS; Khrimian A; Svatos A; Dickens JC; Otalora-Luna F; Kaplan F; Alborn HT; Teal PE;
Address:		"Agriculture Research Service, United States Department of Agriculture, U. S. Horticultural Research Laboratory, 2001 South Rock Road, Fort Pierce, FL 34945, USA. stephen.lapointe@ars.usda.gov"
Journal Title:		J Chem Ecol
Year:		2012
Volume:		20120321
Issue:		4
Page Number:		408 - 417
DOI:		10.1007/s10886-012-0096-8
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"An unsaturated hydroxy-ester pheromone was isolated from the headspace and feces of male Diaprepes abbreviatus, identified, and synthesized. The pheromone, methyl (E)-3-(2-hydroxyethyl)-4-methyl-2-pentenoate, was discovered by gas chromatography-coupled electroantennogram detection (GC-EAD), and identified by gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). The synthesis yielded an 86:14 mixture of methyl (E)-3-(2-hydroxyethyl)-4-methyl-2-pentenoate (active) and methyl (Z)-3-(2-hydroxyethyl)-4-methyl-2-pentenoate (inactive), along with a lactone breakdown product. The activity of the synthetic E-isomer was confirmed by GC-EAD, GC-MS, NMR, and bioassays. No antennal response was observed to the Z-isomer or the lactone. In a two-choice olfactometer bioassay, female D. abbreviatus moved upwind towards the synthetic pheromone or natural pheromone more often compared with clean air. Males showed no clear preference for the synthetic pheromone. This pheromone, alone or in combination with plant volatiles, may play a role in the location of males by female D. abbreviatus"
Keywords:		"Animals Feces/chemistry Female Male Sex Attractants/*analysis/biosynthesis/*chemical synthesis/pharmacology Sexual Behavior, Animal/drug effects Weevils/*metabolism;"
Notes:		"MedlineLapointe, Stephen L Alessandro, Rocco T Robbins, Paul S Khrimian, Ashot Svatos, Ales Dickens, Joseph C Otalora-Luna, Fernando Kaplan, Fatma Alborn, Hans T Teal, Peter E eng 2012/03/22 J Chem Ecol. 2012 Apr; 38(4):408-17. doi: 10.1007/s10886-012-0096-8. Epub 2012 Mar 21"