| Inhibitory effects of glycyrrhetic acid derivatives on 11 beta- and 3 alpha-hydroxysteroid dehydrogenases of rat liver. | |
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MedLine Citation:
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PMID: 1477917 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Glycyrrhetic acid (GA), an aglycone of glycyrrhizin (GL), is a potent inhibitor of 11 beta- and 3 alpha-hydroxysteroid dehydrogenases. 11 beta-Hydroxysteroid dehydrogenase activity of rat liver microsomes was potently inhibited by GA, 3-deoxyglycyrrhetic acid (3-deoxyGA), 3-ketoglycyrrhetic acid (3-ketoGA), 3-epiglycyrrhetic acid (3-epiGA) and 11-deoxoglycyrrhetic acid (11-deoxoGA), with I50 values of 2-4 x 10(-7) M. However, 18 alpha-stereoisomers (I50 = 3-7 x 10(-6) M) of GA, 3-deoxyGA and 11-deoxoGA were one tenth less inhibitory on the enzyme activity than the corresponding 18 beta-isomers. On the other hand, 18 alpha-stereoisomers of GA, 3-deoxyGA and 11-deoxoGA inhibited 3 alpha-hydroxysteroid dehydrogenase activity of rat liver cytosol more potently than the corresponding 18 beta-isomers. I50 values of 18 alpha- and 18 beta-isomers were 2 and 7 x 10(-6) M, respectively, in the case of GA, 8 and 20 x 10(-6) M in 3-deoxyGA, 3 and 20 x 10(-6) M in 11-deoxoGA. These results indicate that the 18 beta-conformation of oleanane is important for the inhibition of 11 beta-hydroxysteroid dehydrogenase but on the contrary the 18 alpha-conformation is important for the inhibition of 3 alpha-hydroxysteroid dehydrogenase. |
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Authors:
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T Akao; T Terasawa; S Hiai; K Kobashi |
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Publication Detail:
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Type: In Vitro; Journal Article |
Journal Detail:
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Title: Chemical & pharmaceutical bulletin Volume: 40 ISSN: 0009-2363 ISO Abbreviation: Chem. Pharm. Bull. Publication Date: 1992 Nov |
Date Detail:
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Created Date: 1993-02-08 Completed Date: 1993-02-08 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0377775 Medline TA: Chem Pharm Bull (Tokyo) Country: JAPAN |
Other Details:
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Languages: eng Pagination: 3021-4 Citation Subset: IM |
Affiliation:
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Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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11-beta-Hydroxysteroid Dehydrogenases 3-Hydroxysteroid Dehydrogenases / antagonists & inhibitors* 3-alpha-Hydroxysteroid Dehydrogenase (B-Specific) Animals Cytosol / enzymology Glycyrrhetinic Acid / analogs & derivatives*, pharmacology Glycyrrhizic Acid Hydroxysteroid Dehydrogenases / antagonists & inhibitors* Liver / drug effects, enzymology* Male Microsomes, Liver / enzymology Rats Rats, Wistar Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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1405-86-3/Glycyrrhizic Acid; 471-53-4/Glycyrrhetinic Acid; EC 1.1.-/3-Hydroxysteroid Dehydrogenases; EC 1.1.-/Hydroxysteroid Dehydrogenases; EC 1.1.1.146/11-beta-Hydroxysteroid Dehydrogenases; EC 1.1.1.50/3-alpha-Hydroxysteroid Dehydrogenase (B-Specific) |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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