Abstract:
:The oxidation of 6-hydroxy-2,2,5,7,8-pentamethylchroman, Trolox C, and alpha-tocopherol by horseradish peroxidase was examined by stopped-flow and ESR experiments. The catalytic intermediate of horseradish peroxidase during the oxidation of vitamin E analogues and vitamin E was invariably Compound II, and rate constants for the rate-determining step decreased in the order 6-hydroxy-2,2,5,7,8-pentamethylchroman > Trolox C > alpha-tocopherol. The formation of phenoxyl radicals from substrates was verified with ESR and was followed optically. Resulting 6-hydroxy-2,2,5,7,8-pentamethylchroman and Trolox C radicals decayed through a dismutation reaction, followed by formation of the quinoid form via a transient intermediate. The sequence of events after formation of 6-hydroxy-2,2,5,7,8-pentamethylchroman and Trolox C radicals was similar to that observed by pulse radiolysis (Thomas, M. J., and Bielski, B. H. J. (1989). J. Am. Chem. Soc. 111, 3315-3319). Final oxidation products of 6-hydroxy-2,2,5,7,8-pentamethylchroman and Trolox C were identified as the quinoid forms and were obtained quantitatively whether or not the analogue had a carboxyl or methyl group at the 2-position of chroman ring. In contrast, enzymatic oxidation of alpha-tocopherol gave alpha-tocopherol quinone in very low yield. Conversion of 6-hydroxy-2,2,5,7,8-pentamethylchroman, Trolox C, and alpha-tocopherol to the corresponding quinones was also catalyzed by metmyoglobin in a reaction completely inhibited by ascorbate.
journal_name
Arch Biochem Biophysjournal_title
Archives of biochemistry and biophysicsauthors
Nakamura M,Hayashi Tdoi
10.1016/0003-9861(92)90280-asubject
Has Abstractpub_date
1992-12-01 00:00:00pages
313-9issue
2eissn
0003-9861issn
1096-0384pii
0003-9861(92)90280-Ajournal_volume
299pub_type
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