Document Detail


Gallate, the component of HIF-inducing catechins, inhibits HIF prolyl hydroxylase.
MedLine Citation:
PMID:  17056012     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Catechins have recently been reported to increase the cellular content of the hypoxia-inducible factor (HIF)-1alpha within mammalian cells. These catechins have a gallate moiety as a common structure. We now report that n-propyl gallate (nPG) also increases the HIF-1alpha protein in the rat heart-derived H9c2 cells. The increase was dose-dependent and reached a maximum at 2-4h after the addition of nPG to the cells. nPG did not change the HIF-1alpha mRNA level, showing that the increase is a posttranscriptional event. Although nPG did not inhibit the HIF prolyl hydroxylase, gallate, the hydrolysis product of nPG, inhibited the enzyme completely at submillimolar concentrations. Model building studies on the human HIF prolyl hydroxylase 2 showed that the two phenolate oxygen atoms of gallate form a chelate with the active site Fe(2+), while the carboxyl group of gallate forms a strong ionic/hydrogen bonding interaction with Arg383, explaining why nPG, which has an esterified carboxyl group, is unable to inhibit the hydroxylase. Together with the observation that gallate was detected in the H9c2 cells treated with nPG, these results suggest that nPG incorporated into the cells is hydrolyzed and the released gallate inhibits the HIF prolyl hydroxylase, thereby reducing the HIF degradation rate and increasing the HIF-1alpha content.
Authors:
Fuyo Tsukiyama; Yumi Nakai; Masataka Yoshida; Takahiro Tokuhara; Kiichi Hirota; Akiko Sakai; Hideyuki Hayashi; Takahiro Katsumata
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2006-10-23
Journal Detail:
Title:  Biochemical and biophysical research communications     Volume:  351     ISSN:  0006-291X     ISO Abbreviation:  Biochem. Biophys. Res. Commun.     Publication Date:  2006 Dec 
Date Detail:
Created Date:  2006-10-31     Completed Date:  2006-12-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0372516     Medline TA:  Biochem Biophys Res Commun     Country:  United States    
Other Details:
Languages:  eng     Pagination:  234-9     Citation Subset:  IM    
Affiliation:
Department of Thoracic and Cardiovascular Surgery, Osaka Medical College, Daigakumachi, Takatsuki 569-8686, Japan.
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MeSH Terms
Descriptor/Qualifier:
Animals
Catechols / chemistry,  metabolism
Cell Line
Computer Simulation
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemistry
Hypoxia-Inducible Factor 1, alpha Subunit / chemistry*,  metabolism*
Models, Biological
Models, Chemical*
Models, Molecular*
Muscle Cells / drug effects,  metabolism*
Procollagen-Proline Dioxygenase / antagonists & inhibitors*
Propyl Gallate / administration & dosage*,  chemistry*
Protein Binding
Protein Conformation
Rats
Chemical
Reg. No./Substance:
0/Catechols; 0/Enzyme Inhibitors; 0/Hif1a protein, mouse; 0/Hypoxia-Inducible Factor 1, alpha Subunit; 120-80-9/catechol; 121-79-9/Propyl Gallate; EC 1.14.11.2/Procollagen-Proline Dioxygenase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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