Investigations of the origins of estrogenic A-ring aromatic

Abstract

The present preliminary study describes an investigation of a putative aromatisation pathway in sewage from cholesterol through the corresponding A-ring aromatic steroid, norcholest-1,3,5(10)-trienol (NCT) to estrone. The synthesis and analytical characterisation of NCT and of the trimethyl silyl ether by gas chromatography-mass spectrometry, is described. The analytical properties of synthetic NCT were used to direct a search for the compound over several months in 1998 in the effluents of two sewage treatment works (STW; Deephams and Harpenden, north London). The study was prompted by the earlier findings that increased vitellogenin concentrations in the plasma of caged male rainbow trout held in the STW effluents (so-called fish ‘feminisation’) could be attributed to the presence of A-ring steroids such as estrone. Until now it has been assumed that these steroids originate from the STW influents and it is not clear to what extent, if at all, aromatisation of steroids might occur during STW operation. NCT was only detected in the solid particles associated with the effluents on one occasion in 8 months. This suggests that the hypothesised pathway is not a major one. Confirmation of previous reports of estrone and 17β-estradiol was also obtained using a published analytical method and by a simple modification of the method these reports were extended to include a regular occurrence of the weaker estrogen, 16α-estriol in the case of Harpenden STW effluents in 1998.