E. Stadler et al., TARSAL CONTACT CHEMORECEPTOR FOR THE HOST MARKING PHEROMONE OF THE CHERRY FRUIT-FLY, RHAGOLETIS-CERASI - RESPONSES TO NATURAL AND SYNTHETICCOMPOUNDS, Physiological entomology, 19(2), 1994, pp. 139-151
The European cherry fruit fly (Rhagoletis cerasi L.; Diptera, Tephriti
dae) marks cherries (Prunus avium L.) after oviposition with a host ma
rking pheromone (HMP). The marking trail prevents additional ovipositi
on by the same or other females into the same fruit. On the ventral si
de of the tarsi of both sexes, contact-chemoreceptor sensilla were ide
ntified which contain a receptor cell selectively sensitive to HMP. Th
e HMP receptors of males were slightly more sensitive than those of fe
males, suggesting that the more general term 'host-marking pheromone'
is more appropriate than the previously used 'oviposition deterring ph
eromone (ODP)'. The four structural isomers of the HMP, glucopyranosyl
)-oxy-8RS-hydroxypalmitoyl)-taurine, and various derivatives were synt
hesized and tested in an electrophysiological bioassay. Both the 8R,15
R and the 8S,15R isomers of the HMP were equally active with a thresho
ld of about 2 x 10(-10) M, and were shown to be present in the female
faeces in similar proportions. The two 15S HMP isomers were about 13 t
imes less active. Testing synthetic derivatives of the HMP molecule re
vealed that the presence of the four moieties of the molecule are impo
rtant for the activity: taurine, palmitic acid, C(8) hydroxyl group, a
nd glucose (C(15)). The chain length of the fatty acid, the hydroxyl g
roup at C(8) and the position of glucose at C(15) also influenced the
activity. Only minor loss of activity (factor 2) relative to the natur
al molecule was observed when the methyl group in the C(15) position w
as removed. The removal of the beta-glycosidically linked glucose (rep
laced by a hydroxyl group) resulted in about a 4-fold loss of activity
. The cation of the HMP molecule seemed to have no effect on its activ
ity, whereas both low and high pH reduced it significantly. Based on t
hese results, field experiments have been initiated to control oviposi
tion by cherry fruit flies on cherries applying the 15-desmethyl-HMP d
erivative.