On the structures of hydroxylated metabolites of estradiol 17-sulfate by rat liver microsomes.
The metabolism of estradiol 17-sulfate (ES) by hepatic microsomes of female rats produced four new metabolites in addition to 2- and 4-hydroxyestradiol 17-sulfates (2- and 4-OH-ES), which were detected on an HPLC chromatogram. By comparison with synthetic specimens, three of these compounds were identified as 6alpha-, 6beta-, and 7beta-hydroxyestradiol 17-sulfates. To elucidate the structure of the remaining metabolite, a large-scale incubation of ES was carried out, followed by isolation using preparative HPLC to give the single material, which was assigned as 15beta-hydroxyestradiol 17-sulfate by instrumental analyses. On the other hand, when ES was incubated with the microsomes of male rats, 2-OH-ES was produced accompanied by two minor products: 4-OH-ES and a metabolite of unknown structure. The results show clearly that the metabolism of ES by rat hepatic microsomes is remarkably different between the sexes.
Itoh
Yoshimi
Y
Hokkaido College of Pharmacy, 7-1 Katsuraoka-cho, Otaru, Hokkaido 047-0264, Japan.
Matsuda
Noriko
N
Matsuura
Keiko
K
Watanabe
Kazuhiro
K
Takanashi
Kaori
K
Itoh
Shinji
S
Takagi
Hidetoshi
H
Yoshizawa
Itsuo
I
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004958:Estradiol / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism*; D005260:Female; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D015394:Molecular Structure; D051381:Rats; D017208:Rats, Wistar; D012727:Sex Characteristics
C048615:estradiol 17-sulfate; D004958:Estradiol