Presence and estrogenicity of anthracene derivatives in coastal Japanese waters.
An analytical method was developed to measure levels of anthracene (ANT) and its derivative compounds 9,10-anthraquinone (ATQ) and eight hydroxy-anthraquinones (hATQs) in seawater from Tokyo Bay and Suruga Bay, Japan. The hATQs produced through photochemical reaction of ANT are known to be toxic. Seawater samples contained ANT at levels ranging from < 0.2 to 4.7 ng/L, ATQ from 3.9 to 200 ng/L, 1-hydroxyanthraquinone (1-hATQ) from < 0.9 to 5.3 ng/L, and 2-hATQ from 1.6 to 5.5 ng/L. The yeast two-hybrid system was also used to evaluate the estrogenic activity of these compounds. Estrogen agonist and antagonist tests with or without rat liver S9 were carried out. Some compounds showed estrogenic activity: The strongest (2-hydroxyanthraquinone) was of similar potency to p-nonylphenol. Concentrations of some estrogenic derivatives in the samples were higher than those of the parent ANT Polycyclic aromatic hydrocarbons (PAHs) such as ANT appear able to be transformed into toxic compounds in the environment when they are irradiated by sunlight, so it is important to monitor not only PAHs but also hydroxyl-PAH-quinones in the environment.
Kurihara
Ryo
R
Laboratory of Ecological Chemistry, Institute for Environmental Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
Shiraishi
Fujio
F
Tanaka
Noriho
N
Hashimoto
Shinya
S
D000873:Anthracenes / Q000494:pharmacology*; D004967:Estrogens / Q000494:pharmacology*; D007564:Japan; D012623:Seawater / Q000737:chemistry*
D000873:Anthracenes; D004967:Estrogens; C034020:anthracene