Transesterification of juvenile hormone occurs in vivo in locust when injected in alcoholic solvents

Catabolism of juvenile hormone was studied in vivo in the African locust by injection of the labelled natural enantiomer (10R) (12-3H) JH-III. Due to the poor solubility of JH in aqueous solution, it was injected in a water-miscible solvent. Ethanol was chosen for its apparently low toxicity towards the locust. In these experimental conditions, reverse phase liquid chromatography procedure (RP-HPLC) coupled with on line radiodetection, revealed an apolar metabolite of JH-III. This compound was found both in adult females and in fifth stadium larvae. We demonstrate that this metabolite resulted from substitution of the carboxyl methyl group of JH-III by some hydrophobic moiety. This compound co-migrates in our RP-HPLC system with the JH analog epoxy-ethyl farnesoate (JH-III ethyl ester) obtained by KCN-catalysed transesterification of JH-III in ethanol. Both JH-III ethyl ester of chemical origin and biological compounds extracted from locusts give the same spectra when analyzed by gas chromatography-mass spectroscopy (GC-MS). Transesterification of JH-III was not observed with locust tissues incubated in vitro but occurred in vivo even if JH was injected in other alcoholic solvents such as propanol. Our data suggest that transesterification of JH-III occurred in vivo and underline the role of injecting solvent in in vivo studies.