ABSTRACT
The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7, 9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R, 9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.
Subject(s)
Alcohols/chemistry , Hymenoptera/physiology , Pheromones/chemistry , Alcohols/metabolism , Animals , Female , Gas Chromatography-Mass Spectrometry , Pheromones/biosynthesisABSTRACT
A gas chromatographic method using electron capture detection for determination of the stereochemical composition of chiralolatile compounds, e.g., pheromones, at the picogram level is described. Substances of interest are analyzed as pentafluorobenzoate derivatives on fused silica capillary columns coated with CP Sil-88. This method was developed primarily for the quantitative analyses of stereoisomerism of the pheromone precursor, diprionol, in female sawflies,Neodiprion sertifer. It was possible to separate the stereoisomers showing (2S, 3S, 7R) and (2S, 3S, 7S) configurations. Resolution of the (2S, 3S, 7S)- and (2S, 3R, 7R)-diastereomers was high enough to allow the quantification of these stereoisomers. A quantitative analysis of the diprionol production in individualN. sertifer females yielded 7.5-9.7 ng/female.
ABSTRACT
The thoracic glands of males in two ant-lion speciesSynclysis baetica andAcanthaclisis occitanica, which occur sympatrically in Israel, were found to contain a volatile secretion with two-component blends of nerol oxide and (R,Z)-6-tridecen-2-ol (approx 1â¶5) and nerol oxide and 10-homonerol oxide (approx. 1â¶2), respectively. Chemical analyses were performed using gas chromatography-mass spectrometry, chiral gas chromatography, and ozonolysis, and the proposed structures were confirmed by synthesis. The species-specific, few-component volatile signals are thought to function as a reproductive isolation mechanism between the two sympatric species. Biochemical relationships between the nerol derivatives and between the unsaturated secondary alcohols are discussed.
ABSTRACT
The thoracic gland of the ant-lionEuroleon nostras was found to contain nerol oxide (1a) and (Z)-6-undecen-2-ol (nostrenol,3) while the speciesGrocus bore contained 10-homonerol oxide (1b) and nostrenol (3). Nerol (2a) and 10-homonerol (2b) were found in a third species,Myrmeleon formicarius. 10-Homonerol, racemic 10-homonerol oxide, and racemic as well as (R)- and (S)-nostrenol were synthesized. The nerol oxide ofE. nostras and the 10-homonerol oxide ofG. bore were found to be racemic, while both species contained optically pure (R)-nostrenol (28).
ABSTRACT
A gas chromatography fraction collector for use with capillary columns, consisting of an all-glass system with a revolving collector housing six capillary tubes, 100 × 1 mm (internal diameter), has been constructed and tested. The collector is cooled with solid CO2 and has a recovering efficiency of 50-75% in the 100-µg to 1-ng range for compounds of different polarities and volatilities, exemplified by mono- and sesquiter-penes and long-chain esters. The technique has been used for fractionating blends of semiochemicals prior to microchemical reactions, spectroscopic analyses, and behavioral experiments.
