Chiu P L, Mushtaq M, Weems H B, Yang S K
Biochem Biophys Res Commun. 1984 Oct 15;124(1):114-20. doi: 10.1016/0006-291x(84)90924-0.
Optically active 7-hydroxy-7,8-dihydrobenzo[a]pyrene and 8-hydroxy-7,8-dihydrobenzo[a]pyrene were identified as two of the major metabolites formed by incubation of 7,8-dihydrobenzo[a]pyrene with rat liver microsomes. Optically active 9-hydroxy-9,10-dihydrobenzo[a]pyrene and 10-hydroxy-9,10-dihydrobenzo[a]pyrene were similarly identified as two of the minor metabolites of 9,10-dihydrobenzo[a]pyrene. The formation of these metabolites was abolished either by prior treatment of liver microsomes with carbon monoxide or the absence of NADPH, but was not inhibited by an epoxide hydrolase inhibitor. The results indicate that the aliphatic carbons of dihydro polycyclic aromatic hydrocarbons may undergo stereoselective hydroxylation reactions catalyzed by the cytochrome P-450 system of rat liver microsomes.
光学活性的7-羟基-7,8-二氢苯并[a]芘和8-羟基-7,8-二氢苯并[a]芘被鉴定为7,8-二氢苯并[a]芘与大鼠肝脏微粒体孵育形成的两种主要代谢产物。光学活性的9-羟基-9,10-二氢苯并[a]芘和10-羟基-9,10-二氢苯并[a]芘同样被鉴定为9,10-二氢苯并[a]芘的两种次要代谢产物。这些代谢产物的形成可通过预先用一氧化碳处理肝脏微粒体或不存在NADPH而消除，但不受环氧水解酶抑制剂的抑制。结果表明，二氢多环芳烃的脂肪族碳可能会发生由大鼠肝脏微粒体细胞色素P-450系统催化的立体选择性羟基化反应。
