RT Journal Article
SR Electronic
T1 Metabolism of 3-tert-butyl-4-hydroxyanisole by horseradish peroxidase and hydrogen peroxide.
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 816
OP 820
VO 20
IS 6
A1 K Tajima
A1 M Hashizaki
A1 K Yamamoto
A1 T Mizutani
YR 1992
UL http://dmd.aspetjournals.org/content/20/6/816.abstract
AB 3-Tert-butyl-4-hydroxyanisole (3-BHA) was metabolized in the presence of horseradish peroxidase and hydrogen peroxide to 2-tert-butyl-p-benzoquinone (TBQ), 2,3-epoxy-5-tert-butyl-1,4-benzoquinone (TBQ-epoxide), and two known dimers. The formation of TBQ from 3-BHA required both horseradish peroxidase and hydrogen peroxide. When 2.5 mM 3-BHA was incubated with horseradish peroxidase and hydrogen peroxide, the formation of TBQ increased with hydrogen peroxide concentration up to 5 mM and decreased gradually at higher concentrations of hydrogen peroxide. On the other hand, the formation of TBQ-epoxide from 3-BHA increased, depending on hydrogen peroxide concentration at higher concentrations than 1 mM. In incubating 2-tert-butylhydroquinone (TBHQ) with horseradish peroxidase and hydrogen peroxide, TBHQ was rapidly oxidized to TBQ, and then TBQ-epoxide was also produced at concentrations more than 2.5 mM of hydrogen peroxide. In the absence of horseradish peroxidase, the incubation of TBQ with hydrogen peroxide resulted in TBQ-epoxide production. These results suggest that 3-BHA is metabolized to TBHQ, which is rapidly oxidized to TBQ, by horseradish peroxidase and hydrogen peroxide, and then TBQ is converted to TBQ-epoxide by only hydrogen peroxide.