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J.Health Sci., 50(5), 556-560, 2004
Novel Estrogenic Microsomal Metabolites from Phthalate Esters
Yoshinori Okamoto, Kana Okajima, Chitose Toda, Koji Ueda, Kiyomatsu Hashizume, Kazuo Itoh,
and Nakao Kojima*
Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan
Many researchers have found evidence of the
estrogenic effects of phthalate esters (PEs), but the
disruption mechanism is not fully elucidated. Once PEs
are hydroxylated at the ring 4-position, the resulting
compounds exhibit unequivocal binding affinity for
human estrogen receptors. In this study, we first
succeeded to demonstrate the generation of potent
estrogenic metabolite from PEs. We used rat liver
microsomes and dimethyl phthalate (DMP) as a
representative for the metabolism of PEs. Among the
metabolites detected by HPLC, one of them was
consistent with an authentic compound, 4-hydroxylated DMP
(DMP-4OH) on their HPLC profiles. Together with the
UV (lambda max = 257 nm) and MS
(m/z 210) data, the metabolite was concluded to be DMP-4OH. We propose
that this ring-hydroxylated metabolite could be a key
active species in the endocrine disrupting processes of
PEs.
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