title: Hydroxylated PAHs alter the synthesis of androgens and estrogens in subcellular fractions of carp gonads.
abstract: 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.
authors: Environmental Chemistry Department, IDAEA-CSIC-, Jordi Girona 18, 08034 Barcelona, Spain. deniseferna@gmail.com
authors: Denise
authors: D
authors: Fernandes
authors: Cinta
authors: C
authors: Porte
mesh_terms: D043209:11-beta-Hydroxysteroid Dehydrogenase Type 2 / Q000378:metabolism; D000728:Androgens / Q000378:metabolism*; D000736:Androstenes / Q000378:metabolism; D000818:Animals; D001141:Aromatase / Q000378:metabolism; D002347:Carps; D002911:Chrysenes / Q000378:metabolism / Q000633:toxicity; D004967:Estrogens / Q000378:metabolism*; D005260:Female; D006900:Hydroxylation; D008297:Male; D008928:Mitochondria / Q000187:drug effects / Q000378:metabolism; D010053:Ovary / Q000187:drug effects* / Q000378:metabolism; D010616:Phenanthrenes / Q000378:metabolism / Q000633:toxicity; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D011721:Pyrenes / Q000378:metabolism / Q000633:toxicity; D013254:Steroid 17-alpha-Hydroxylase / Q000037:antagonists & inhibitors / Q000378:metabolism; D013347:Subcellular Fractions; D013737:Testis / Q000187:drug effects* / Q000378:metabolism; D018675:Toxicity Tests; D014874:Water Pollutants, Chemical / Q000633:toxicity*
chemical_list: D000728:Androgens; D000736:Androstenes; D002911:Chrysenes; D004967:Estrogens; D010616:Phenanthrenes; D011084:Polycyclic Aromatic Hydrocarbons; D011721:Pyrenes; D014874:Water Pollutants, Chemical; C091375:9-phenanthrol; C011657:adrenosterone; D043209:11-beta-Hydroxysteroid Dehydrogenase Type 2; D001141:Aromatase; D013254:Steroid 17-alpha-Hydroxylase; C033146:1-hydroxypyrene