New type of Sesiidae sex pheromone identified from the hornet moth Sesia apiformis.
Two components of the female-produced sex pheromone of the hornet moth, Sesia apiformis, were identified as (3Z,13Z)-octadeca-3,13-dien-1-ol (3Z,13Z-18:OH) and (2E,13Z)-octadeca-2,13-dienal (2E,13Z-18:Al), a pheromone structure new in Sesiidae. Pooled gland extracts showed the two major compounds in a proportion of ca. 2:3, while SPME-investigations on single calling females revealed a ratio of ca. 1:7. Although the single compounds were not attractive, a 2:3 mixture proved to be highly active towards males in field tests. Small amounts of (2E,13Z)-octadecadienol (2E,13Z-18:OH) were found in the sex pheromone gland of females, however, the biological significance of the compound remains unclear. Methyl sulfide was found to readily react with 2-alkenals, providing an effective new method for the characterization of this type of compound upon GC/MS. The derivatives, 1,1,3-tris(methylthio)alkanes, are the products of the addition of methyl sulfide to the double bond and the transformation of the carbonyl group into the corresponding bis(methylthio)acetal. The mass spectra of these compounds are characterized by diagnostic signals at m/z 107 and/or m/z 121. These fragments represent the first carbon unit or the first two carbon units of the derivative, respectively. The parent signal in the spectra of thiomethyl derivatives of 2-alkenals showing no other double bonds is represented by m/z M+ - 121, formed upon loss of the first two carbon units. By employing a solution of methyl sulfide in dimethyl sulfide, the double bond positions in 2E,13Z-18:Al could be fully characterized by GC/MS.
Francke
W
W
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany. francke@chemie.uni-hamburg.de
Karalius
V
V
Plass
E
E
Lehmann
L
L
Dos Santos
A
A
Buda
V
V
Borg-Karlson
A K
AK
Mozuraitis
R
R
D000447:Aldehydes / Q000032:analysis*; D000818:Animals; D003718:Denmark; D005233:Fatty Alcohols / Q000032:analysis*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D008097:Lithuania; D008297:Male; D009036:Moths / Q000737:chemistry* / Q000502:physiology*; D012724:Sex Attractants / Q000737:chemistry* / Q000302:isolation & purification; D012726:Sexual Behavior, Animal / Q000502:physiology; D013045:Species Specificity
D000447:Aldehydes; D005233:Fatty Alcohols; D012724:Sex Attractants; C497340:octadeca-2,13-dienal; C497339:octadeca-3,13-dien-1-ol