On the Inhibitory Effect of C_<17>-Sulfoconjugated Catechol Estrogens upon Lipid Peroxidation of Rat Liver Microsomes

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The antioxidant effect of C_<17>-sulfoconjugated catechol estrogens was examined under ascorbic acid-or NADPH-dependent lipid peroxidation in rat liver microsomes and compared with that of various estrogens and α-tocopherol. Among the estrogens tested, a free catechol estrogen such as 4-hydroxyestradiol showed the strongest effect, followed by 2-hydroxyestradiol, 2-methoxyestradiol and estradiol. Next to these steroids, 2-hydroxyestradiol 17-sulfate, followed by 4-methoxyestradiol, 4-hydroxyestradiol 17-sulfate and estrone also showed a strong inhibitory effect, which was greater than that of α-tocopherol. Among the C_<17>-sulfates, the guaiacols (2-and 4-methoxyestradiol 17-sulfate) showed a slightly lower effect than α-tocopherol, but estradiol 17-sulfate had almost no effect. The antioxidant activity observed in phenolic or guaiacol steroids was considered to be attributed to the catechols produced by their 2-(or 4-) hydroxylation or their O-demethylation, respectively, during the incubation. This was confirmed by identification of the catechols produced from phenolic or guaiacol estrogens and even from the estrogen C_3-sulfates. The mechanism of the inhibition by catechols on lipid peroxidation was speculated to involve their activity as radical scavengers, because of their strong reducing activity for 1,1-diphenyl-2-picrylhydrazyl. The above results suggest that C_<17>-sulfoconjugated catechol estrogens (2-and 4-hydroxyestradiol 17-sulfate), although with slightly lower activity than their free catechols, are promising endogenous antioxidants. The physiological role of these estrogen conjugates during pregnancy is discussed.
社団法人日本薬学会の論文
1995-08-15

On the Inhibitory Effect of C_<17>-Sulfoconjugated Catechol Estrogens upon Lipid Peroxidation of Rat Liver Microsomes

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