Document Detail


Aromatase and testosterone fatty acid esters: the search for a cryptic biosynthetic pathway to estradiol esters.
MedLine Citation:
PMID:  1455454     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The estradiol fatty acid esters (lipoidal derivatives, LE2) are extremely potent estrogens that accumulate in fat, including fat of menopausal women. These steroidal esters are protected from metabolism and are converted to the free, biologically active steroid through the action of esterases. Previous studies have shown that biosynthetic pathways in the adrenal gland exist in which steroid fatty acid esters are substrates. This led us to determine whether a cryptic aromatase pathway exists in which testosterone esters could be converted directly into LE2. We tested a representative fatty acid ester, testosterone stearate, both as an inhibitor and as a substrate for the aromatase enzyme from human placental microsomes. This ester had neither activity. In addition, we tested [1 beta-3H]testosterone acetate as a substrate for this enzyme complex, measuring the production of 3H2O as evidence of aromatization. Although the rate of reaction was considerably slower than that of testosterone, 3H2O was produced. However, when [2, 4, 6, 7-3H]testosterone acetate was incubated and the steroidal products isolated, we found that hydrolysis of the substrate had occurred. Both [3H]-labeled testosterone and estradiol were found, and very little if any [3H]estradiol acetate was formed. Thus, we conclude that an aromatase pathway involving testosterone esters does not exist and that the sole source of LE2 is through direct esterification of estradiol.
Authors:
J M Larner; S L Pahuja; V M Brown; R B Hochberg
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Steroids     Volume:  57     ISSN:  0039-128X     ISO Abbreviation:  Steroids     Publication Date:  1992 Oct 
Date Detail:
Created Date:  1993-01-06     Completed Date:  1993-01-06     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0404536     Medline TA:  Steroids     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  475-9     Citation Subset:  IM    
Affiliation:
Department of Obstetrics and Gynecology, Yale University School of Medicine, New Haven, Connecticut 06510.
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MeSH Terms
Descriptor/Qualifier:
Aromatase / chemistry*
Esters / metabolism
Estradiol / chemistry*
Fatty Acids / chemistry*
Substrate Specificity
Testosterone / chemistry*
Grant Support
ID/Acronym/Agency:
CA29591/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Esters; 0/Fatty Acids; 50-28-2/Estradiol; 58-22-0/Testosterone; EC 1.14.14.1/Aromatase

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


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