Metabolism of (S)-bioallethrin and related compounds in humans

Chrysanthemate insecticides like (S)-bioallethrin, natural pyrethins, and r elated pyrethroids are subjected to extensive hydrolytic and oxidative dege neration by the mammalian metabolism, leading to a complex series of metabo lites partially conjugated and finally eliminated in the urine. The major o xidation products of chrysanthemic acid, cis-(E)- and trans-(E)-chrysanthem umdicarboxcylic acid (cis-(E) and trans-(E)-CDCA), were synthesized and the ir structures were established by nuclear magnetic resonance spectrometry ( H-1-NMR) and mass spectrometry (MS). Diastereoselective separation was by h igh performance liquid chromatography (HPLC) and capillary gas chromatograp hy (GC). An analytical method for extraction and identification of CDCA fro m human urine was developed. Quantitation was by gas chromatography and ele ctron-impact mass spectrometry (GC/MS). The limit of detection was 20 mu g/ l for cis-(E)-CDCA and 10 mu g/l for trans-(E)-CDCA. To test the applicabil ity of the presented method, urine samples of humans exposed to (S)-bioalle thrin were investigated. Urinary peak excretion of trans-(E)-CDCA occurred within 24 h after exposure. (C) 1999 Elsevier Science Ireland Ltd. All righ ts reserved.