Novel metabolic pathway of phenols catalyzed by cytochrome P450 and its mechanism

We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substitue nt = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted wi th rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chlor ide model system, the substituent was eliminated to produce hydroquinone. I n the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the pr oduct derived from the eliminated group. Results indicated that the mechani sm of this reaction can be divided into two types: the substituent is elimi nated as an anion and as a cation. P450 also catalyzed phenol coupling reac tion to give biphenyl derivatives, diphenyl ether derivatives, and dibenzod ioxin.