Identification of the steroid fatty acid ester conjugates formed in vivo in Mytilus edulis as a result of exposure to estrogens

Labadie, Pierre, Peck, Mika, Minier, Christophe and Hill, Elizabeth M (2007) Identification of the steroid fatty acid ester conjugates formed in vivo in Mytilus edulis as a result of exposure to estrogens. Steroids, 72 (1). pp. 41-49. ISSN 0039-128X

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Vertebrate-type sex steroids have been detected in a number of mollusk species and may play a role in the reproductive physiology of the animal. Mollusks are also exposed to exogenous estrogenic steroids that are present in sewage effluents, and these may add to the estrogenic burden of exposed animals. We investigated the uptake of estrogens in the blue mussel, Mytlius edulis and report for the first time the identity of estrogen fatty acid ester metabolites formed in vivo in an invertebrate. We exposed mussels to waterborne radiolabeled [14C]-17ß-estradiol (E2) or estrone (E1) and determined the nature of their metabolites using radio-HPLC and mass spectrometry (MS). After 13 days of exposure to 10 ng/L E2, concentrations of radiolabeled residues were 2428-fold higher in M. edulis soft tissues compared with the ambient water concentration of E2. All the E2 residues in the mussel were present as a lipophilic ester which, in depuration studies, had a half-life of 8.3 days. Exposure of mussels to [14C]-E1 (70 ng/L) resulted in formation of a similar lipophilic metabolite that after hydrolysis released [14C]-E2. Tandem MSMS analyses of the purified steroid ester fraction isolated from mussels exposed to either E2 or E1 revealed that they had the same composition and comprised C16:0, C16:1 and C16:2 esters of E2. This work reveals that in vivo E1 is rapidly metabolized to E2 in mussels prior to conjugation to C16 fatty acid esters, proving that C17-ketoreductase and C16 fatty acid acyl-CoA:E2 acyltransferase are important enzymes for the metabolism of estrogens in M. edulis.

Item Type: Article
Additional Information: First identification of the metabolites of estrogens formed in mussels exposed to environmental concentrations of estrogens. MP designed and carried out lab analysis and wrote paper with EH & LP. LP carried out GCMS analysis.
Schools and Departments: School of Life Sciences > Evolution, Behaviour and Environment
Depositing User: Mika Peck
Date Deposited: 06 Feb 2012 18:20
Last Modified: 20 Mar 2012 10:12
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