Enantiomeric composition of grandisol and grandisal produced by Pissodes strobi and P. nemorensis and their electroantennogram response to pure enantiomers

Abstract

Grandisol (cis-2-isopropenyl-1-methylcyclobutaneethanol) and its corresponding aldehyde, grandisal, were previously isolated and identified as aggregation pheromone components for Pissodes strobi (Peck) and P. nemorensis Germar, but the enantiomeric ratios produced by these insects were not previously determined. We isolated grandisol and grandisal from males of both P. strobi and P. nemorensis. The insect-produced grandisol was derivatized with trifluoroacetic anhydride, and the enantiomeric composition was determined by gas chromatography on an optically active cyclodextrin glass capillary column. The insect-produced grandisal was first reduced to grandisol before derivatization. P. nemorensis produced nearly 100% (1 R,2 S)-grandisol and nearly 100% (1 S,2 R)-grandisal. P. strobi produced 99% (1 R,2 S)-grandisol and approximately 60% (lR,2S)-grandisal. In electroantennogram (EAG) studies with live P. nemorensis and P. strobi, no significant differences were found between the responses of males and females to racemic grandisol, racemic grandisal, or the 1R,2S and 1S,2R enantiomers of grandisol and grandisal, which is consistent with previous assertions that these compounds are aggregation pheromones. Although no studies to date with P. strobi have demonstrated a behavioral response to grandisol and grandisal, P. strobi antennae detected all enantiomers of grandisol and grandisal tested in EAG tests. The antennae of P. nemorensis responded significantly more to (1 R,2 S) grandisal than to (1 S,2 R)-grandisal, despite producing only (1 S,2 R)-grandisal. © 1993 Plenum Publishing Corporation.