Cerniglia C E, Gibson D T
J Biol Chem. 1979 Dec 10;254(23):12174-80.
Cunninghamella elegans oxidized benzo[a]pyrene to several metabolic products. Compounds that were isolated and identified were: trans-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene, trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene, benzo[a]pyrene 1,6-quinone, benzo[a]pyrene 3,6-quinone, 9-hydroxybenz[a]pyrene, and 3-hydroxybenzo[a]pyrene. In addition, an unidentified dihydroxybenzo[a]pyrene metabolite was also formed. Experiments with [14C]benzo[a]pyrene showed that over a 96-h period, 18.4% of the hydrocarbon was converted to metabolic products. Most of the metabolites were sulfate conjugates as demonstrated by the formation of benzo[a]pyrene quinones and phenols after treatment with aryl sulfatase. Glucuronide and sulfate conjugates were also detected as water-soluble metabolites. The results show that benzo[a]pyrene is metabolized by a filamentous fungus in a manner that is remarkably similar to that observed in higher organisms.
华美小克银汉霉将苯并[a]芘氧化为多种代谢产物。分离并鉴定出的化合物有：反式-9,10-二羟基-9,10-二氢苯并[a]芘、反式-7,8-二羟基-7,8-二氢苯并[a]芘、苯并[a]芘1,6-醌、苯并[a]芘3,6-醌、9-羟基苯并[a]芘和3-羟基苯并[a]芘。此外，还形成了一种未鉴定的二羟基苯并[a]芘代谢产物。用[14C]苯并[a]芘进行的实验表明，在96小时内，18.4%的碳氢化合物转化为代谢产物。如用芳基硫酸酯酶处理后形成苯并[a]芘醌和酚类所示，大多数代谢产物是硫酸酯结合物。葡糖醛酸和硫酸酯结合物也被检测为水溶性代谢产物。结果表明，丝状真菌对苯并[a]芘的代谢方式与在高等生物中观察到的方式非常相似。
