A novel estrogenic compound transformed from fenthion under UV-A irradiation

The photo-transformed products of fenthion well-known as one of the most photosensitive organophosphorus insecticides and their estrogenic activities were investigated using a yeast two-hybrid assay incorporating the human estrogen receptor alpha (hERalpha). We identified fenthion sulfoxide and 3-methyl-4-methylsulfinylphenol (MMS) as the major transformed products and 3-methyl-4-(methylthio)phenol (MMP) as the minor product under UV-A irradiation. Further, significant estrogenic activity was observed in the solution irradiated for 160 min; this activity was evaluated as 18 pM converted to 17beta-estradiol (E(2)) equivalent concentration. By using authentic standards, it was found that MMP possessed weak estrogenic activity; its activity was evaluated as 1.7x10(-6) times compared with that of E(2). However, it was also revealed that the activity due to MMP was only 13%. From high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopies, we newly identified a significant estrogenic compound transformed from fenthion, O,O-dimethyl S-[3-methyl-4-(methylthio)phenyl]phosphorothioate, S-aryl fenthion.