Comparison of estrogen-derived ortho-quinone and para-quinol concerning induction of oxidative stress.
Ortho-quinones formed from catechol estrogens are considered prooxidants due to the production of superoxide radical anions through redox cycling via semiquinones. Para-quinols have been identified as novel metabolites of and as the major products of hydroxyl-radical scavenging by estrogens. Cycling of these compounds has also been discovered, because they are converted back to the parent estrogen via reductive aromatization in vitro and in vivo. We hypothesized that, unlike ortho-quinones, para-quinols do not induce oxidative stress due to this cycling. Like the estrogen itself, the 17beta-estradiol-derived para-quinol (10beta,17beta-dihydroxyestra-1,4-diene-3-one) did not induce oxidative stress, as the rate of hydrogen peroxide production during the incubations of the compounds in various tissue homogenates was not significantly different from that of the control experiments performed without the addition of a test compound. We also confirmed that the estrogen metabolite estra-1,5(10)-dien-3,4,17-trione (estrone 3,4-quinone) was a profound prooxidant due to redox cycling, especially in uterine tissue. Therefore, we concluded that para-quinols do not induce oxidative stress.
Rivera-Portalatin
Nilka M
NM
Department of Medicinal Chemistry, College of Pharmacy, University of Florida, Gainesville, FL 32610-0485, USA.
Vera-Serrano
José L
JL
Prokai-Tatrai
Katalin
K
Prokai
Laszlo
L
D016227:Benzoquinones / Q000494:pharmacology*; D002853:Chromatography, Liquid; D004967:Estrogens / Q000737:chemistry*; D006873:Hydroquinones / Q000494:pharmacology*; D018384:Oxidative Stress; D053719:Tandem Mass Spectrometry
D016227:Benzoquinones; D004967:Estrogens; D006873:Hydroquinones; C004532:quinone