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Persistence and Pathways of Testosterone Dissipation in Agricultural Soil

Southern Crop Protection and Food Research Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, ON, Canada N5V 4T3

View larger version (20K): [in a new window]   Fig. 1. Structures of testosterone and transformation products detected in soil. Commercially purchased radiolabeled testosterone was substituted with 3H atoms in Positions 1, 2, 6, and 7, or a 14C atom in Position 4.

View larger version (21K): [in a new window]   Fig. 2. Persistence of testosterone in three different soils. [14C]-Testosterone at an initial concentration of 1 mg/kg soil was mineralized to 14CO2 (top panel), total 14C residues in soil extracts were determined by liquid scintillation counting (LSC) (middle panel), and loss of androgenic activity in soil extracts was measured using a human androgen receptor recombinant yeast strain (bottom panel). Note the different time scale in the top panel.

View larger version (25K): [in a new window]   Fig. 3. The effect of soil moisture content on the mineralization of [1,2,6,7–3H(N)]-testosterone. Soils were adjusted to the indicated moisture contents, and the radioactivity in soil extracts before (top panel) and after (bottom panel) evaporation was determined. The difference is taken to be due to evaporative loss of 3H2O produced by the mineralization of testosterone.

View larger version (25K): [in a new window]   Fig. 4. The effect of temperature on testosterone dissipation and disposition of radioactive transformation products. Soils were incubated at the indicated temperatures, and the percent extractable radioactivity was measured as testosterone or products with the indicated high performance liquid chromatography (HPLC)–radioactivity detection (RD) retention times (RT). These correspond to 4-androstene-3,17-dione (26 min); 5-androstan-3,17-dione (39.9 min); and 1,4-androstadiene-3,17-dione (18.9 min).

View larger version (24K): [in a new window]   Fig. 5. The relative androgenic potencies in the yeast androgen receptor gene transcription assay of analytical standards of testosterone, and testosterone transformation products identified in soil extracts.

View larger version (22K): [in a new window]   Fig. 6. Dissipation of 1 mg [1,2,6,7–3H(N)]-testosterone/kg autoclaved loam soil incubated at 30°C. Total radioactivity in extracts was determined by liquid scintillation counting (LSC), while high performance liquid chromatography (HPLC)–radioactivity detection (RD) was used to determine the distribution of radioactivity in testosterone or 4-androstene-3,17-dione, the only detectable transformation product. Androgenic activity in soil extracts was determined with the yeast androgen receptor gene transcription assay.