Journal
STEROIDS
Volume 73, Issue 3, Pages 280-288Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2007.10.011
Keywords
17 beta-butoxy-1,3,5(10)-estratrien-3-ol; antioxidant neuroprotection; chemical shield; steroidal paro-quinol; hydroxyl radical; oxidative stress
Funding
- NCRR NIH HHS [S10 RR012023-01, RR 12028] Funding Source: Medline
- NINDS NIH HHS [NS 44765, R01 NS044765-05, R01 NS044765-01, R01 NS044765, R01 NS044765-04, R01 NS044765-02, R01 NS044765-02S1, R01 NS044765-03] Funding Source: Medline
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Antioxidant action is an important component of the complex neuroprotective effect of estrogens. Combining theoretical prediction and subsequent experimental confirmation by chemical and in vitro paradigms, this study focused on the mechanistic aspects of hydroxyl radical scavenging by 17 beta-butoxy-1,3,5(10)-estratrien-3-ol, a synthetic derivative of 17 beta-estradiol with increased potency to inhibit lipid peroxidation and reduced affinity to estrogen-receptors compared to the endogenous hormone. In the process that acts as a chemical shield, the phenolic A-ring turns into 10 beta-hydroxy-17 beta-butoxy-1,3,5(10)-estratrien-3-one, a non-aromatic paro-quinol, upon capturing hydroxyl radicals, which results in the complete loss of estrogen-receptor affinity and antioxidant activity. However, the parent compound is apparently recovered in brain tissue from this para-quinol via enzyme-catalyzed NAD(P)H-dependent reductive aromatization without causing oxidative stress. Taken together, our report argues for a previously unrecognized antioxidant cycle for estrogen-derived compounds. (C) 2007 Elsevier Inc. All rights reserved.
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