« Previous AbstractFemale sex pheromone components ofHeliothis peltigera (Lepidoptera: Noctuidae) : Chemical identification from gland extracts and male response    Next AbstractAntennal response and field attraction of the predator Elatophilus hebraicus (Hemiptera: Anthocoridae) to sex pheromones and analogues of three Matsucoccus spp. (Homoptera: Matsucoccidae) »

J Chem Ecol

Title:		"Chirality of israeli pine bast scale,Matsucoccus josephi (homoptera: Matsucoccidae) sex pheromone"
Author(s):		Dunkelblum E; Gries R; Gries G; Mori K; Mendel Z;
Address:		"Institute of Plant Protection, Volcani Center, 50250, Bet Dagar, Israel"
Journal Title:		J Chem Ecol
Year:		1995
Volume:		21
Issue:		6
Page Number:		849 - 858
DOI:		10.1007/BF02033465
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"The absolute configuration of the sex pheromone of the Israeli pine bast scale,Matsucoccus josephi, was determined as (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated here asR-E with 10% (2E,5S,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated asS-E. The chirality of the quantitatively minorZ isomer was (2E,5R,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one (R-Z). Chiral assignments were made by comparative gas chromatographic (GC) analysis of naturalM. josephi pheromone with stereoselectively synthesized stereoisomers on a chiral Cyclodex-B column, which separated the enantiomers with baseline resolution. In gas chromatographic-electroantennographic detection (GC-EAD) analysis of the racemicZ andE isomers, the latter elicited the stronger antennal response by maleM. josephi. In GC-EAD of all four stereoisomers, employing the chiral column,R-E was the most active stereoisomer. In field testsR-E attracted 10 times more males ofM. josephi than didS-E. The racemicE/Z pheromone mixture, containing all four stereoisomers in approximately equal amounts, attracted as many maleM. josephi as did an equivalent amount ofR-E, indicating that the other stereoisomers are not inhibitory. The same keto-diene moiety with the same chiral center and configuration in all three known Matsucoccidae sex pheromones implies a common biosynthetic pathway and phylogenetic relationship"
Keywords:
Notes:		"PubMed-not-MEDLINEDunkelblum, E Gries, R Gries, G Mori, K Mendel, Z eng 1995/06/01 J Chem Ecol. 1995 Jun; 21(6):849-58. doi: 10.1007/BF02033465"