Hodgson R M, Seidel A, Bochnitschek W, Glatt H R, Oesch F, Grover P L
Carcinogenesis. 1986 Dec;7(12):2095-8. doi: 10.1093/carcin/7.12.2095.
Metabolic activation of chrysene in mouse skin appears to involve r-1,t-2-dihydroxy-t-3,4-oxy-1,2,3,4-tetrahydrochrysene (anti-chrysene-1,2-diol 3,4-oxide) and 9-hydroxy-r-1,t-2-dihydroxy-t-3,4-oxy-1,2,3,4-tetrahydrochrysene (anti-9-OH-chrysene-1,2-diol 3,4-oxide). The enzyme-catalysed conjugation of these epoxides with [35S]glutathione has been studied in experiments in which the glutathione conjugates were separated by h.p.l.c. and examined by fluorescence spectrophotometry. Both anti-chrysene-1,2-diol 3,4-oxide and anti-9-OH-chrysene-1,2-diol 3,4-oxide formed conjugates nonenzymically and both were shown to be substrates for rat liver glutathione transferases. When anti-chrysene-1,2-diol 3,4-oxide was incubated with [35S]glutathione and a rat liver microsomal metabolizing system, glutathione conjugates with h.p.l.c. and fluorescence spectral characteristics identical to those of conjugates formed from both anti-chrysene-1,2-diol 3,4-oxide and anti-9-OH-chrysene-1,2-diol 3,4-oxide were detected. This finding provides evidence that anti-chrysene-1,2-diol 3,4-oxide can be further metabolized to the triol-epoxide, anti-9-OH-chrysene-1,2-diol 3,4-oxide by rat liver microsomal systems.
在小鼠皮肤中，屈的代谢活化似乎涉及r-1,t-2-二羟基-t-3,4-氧代-1,2,3,4-四氢屈（反式-屈-1,2-二醇3,4-氧化物）和9-羟基-r-1,t-2-二羟基-t-3,4-氧代-1,2,3,4-四氢屈（反式-9-羟基-屈-1,2-二醇3,4-氧化物）。在实验中研究了这些环氧化物与[35S]谷胱甘肽的酶催化结合，其中谷胱甘肽结合物通过高效液相色谱法分离并用荧光分光光度法检测。反式-屈-1,2-二醇3,4-氧化物和反式-9-羟基-屈-1,2-二醇3,4-氧化物均非酶促形成结合物，并且两者均被证明是大鼠肝脏谷胱甘肽转移酶的底物。当将反式-屈-1,2-二醇3,4-氧化物与[35S]谷胱甘肽和大鼠肝脏微粒体代谢系统一起孵育时，检测到具有与由反式-屈-1,2-二醇3,4-氧化物和反式-9-羟基-屈-1,2-二醇3,4-氧化物形成的结合物相同的高效液相色谱和荧光光谱特征的谷胱甘肽结合物。这一发现提供了证据，表明反式-屈-1,2-二醇3,4-氧化物可被大鼠肝脏微粒体系统进一步代谢为三醇环氧化物，即反式-9-羟基-屈-1,2-二醇3,4-氧化物。
