adrenosterone and 9-phenanthrol

Four different polycyclic aromatic hydrocarbons (naphthalene, phenanthrene, pyrene, chrysene) and their hydroxylated metabolites (1-hydroxynaphthalene, 9-hydroxy-phenanthrene, 1-hydroxypyrene, 1-hydroxychrysene) were investigated for their ability to alter the synthesis of steroids by testes and ovaries of the carp Cyprinus carpio. Parental compounds had no significant effect on C17,20-lyase (CYP17), CYP11β and 11β-HSD catalyzed activities, all of them involved in the synthesis of active androgens in carp testes. Conversely, hydroxylated metabolites significantly inhibited C17,20-lyase and CYP11β activities; the strongest inhibitor was 9-hydroxyphenanthrene with IC50s of 10.8 and 31.3 μM for CYP17 and CYP11β, respectively. As for the biosynthesis of estrogens, only 9-hydroxyphenanthrene had a significant inhibitory effect on ovarian CYP19 activity (IC50: 4.3 μM). The study highlights the potential of hydroxylated-polycyclic aromatic hydrocarbons, and particularly 9-hydroxyphenanthrene, to disrupt the synthesis of androgens and estrogens in carp gonads.

Topics: 11-beta-Hydroxysteroid Dehydrogenase Type 2; Androgens; Androstenes; Animals; Aromatase; Carps; Chrysenes; Estrogens; Female; Hydroxylation; Male; Mitochondria; Ovary; Phenanthrenes; Polycyclic Aromatic Hydrocarbons; Pyrenes; Steroid 17-alpha-Hydroxylase; Subcellular Fractions; Testis; Toxicity Tests; Water Pollutants, Chemical