Document Detail


Metabolic activation of the proestrogens trans-stilbene and trans-stilbene oxide by rat liver microsomes.
MedLine Citation:
PMID:  10936078     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A liver microsome-mediated activation of the proestrogens trans-stilbene and trans-stilbene oxide was found in this study. trans-Stilbene and trans-stilbene oxide were negative in estrogen reporter assay using estrogen-responsive human breast cancer cell line MCF-7 and growth assay in rat pituitary tumor cell line MtT/E-2. However, these compounds exhibited estrogenic activity after incubation with liver microsomes of 3-methylcholanthrene-treated rats in the presence of NADPH. In contrast, cis-stilbene and cis-stilbene oxide did not show estrogenic activity after such incubation. When trans-stilbene was incubated with the liver microsomes of 3-methylcholanthrene-treated rats in the presence of NADPH, two metabolites were detected by HPLC. They were identified unequivocally as trans-4-hydroxystilbene and trans-4, 4'-dihydroxystilbene by mass and UV spectral comparison with authentic samples. The oxidase activity of the liver microsomes toward trans-stilbene was inhibited by SKF 525-A and alpha -naphthoflavone. Minor activity was observed when liver microsomes of untreated or phenobarbital-treated rats were used instead of those from 3-methylcholanthrene-treated rats. trans-4-Hydroxystilbene and trans-4,4'-dihydroxystilbene exhibited significant estrogenic activities. These results suggest that the estrogenic activities of trans-stilbene and trans-stilbene oxide were due to formation of hydroxylated metabolites.
Authors:
K Sugihara; S Kitamura; S Sanoh; S Ohta; N Fujimoto; S Maruyama; A Ito
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Toxicology and applied pharmacology     Volume:  167     ISSN:  0041-008X     ISO Abbreviation:  Toxicol. Appl. Pharmacol.     Publication Date:  2000 Aug 
Date Detail:
Created Date:  2000-09-14     Completed Date:  2000-09-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0416575     Medline TA:  Toxicol Appl Pharmacol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  46-54     Citation Subset:  IM    
Copyright Information:
Copyright 2000 Academic Press.
Affiliation:
Institute of Pharmaceutical Science, Department of Cancer Research, Research Institute for Radiation Biology and Medicine, Hiroshima University School of Medicine, Hiroshima University, Kasumi 1-2-3, Minami-ku, Hiroshima, 734-8551, Japan.
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MeSH Terms
Descriptor/Qualifier:
Animals
Biotransformation
Estrogens / toxicity
Humans
Male
Microsomes, Liver / metabolism*
Rats
Rats, Sprague-Dawley
Stilbenes / pharmacokinetics*,  toxicity
Tumor Cells, Cultured
Chemical
Reg. No./Substance:
0/Estrogens; 0/Stilbenes; 17619-97-5/stilbene oxide

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