Exposure to petrogenic polycyclic aromatic hydrocarbons (PPAHs) is the major human health hazard associated with the Deepwater Horizon oil spill. Alkylated phenanthrenes are the most abundant PPAHs present in the crude oil and could contaminate the food chain. We describe the metabolism of a C₁-phenanthrene regioisomer 1-methylphenanthrene (1-MP) and a C₂-phenanthrene regioisomer 9-ethylphenanthrene (9-EP) in human HepG2 cells. The structures of the metabolites were identified by HPLC-UV-fluorescence detection and LC-MS/MS. Side chain hydroxylation of 1-MP and 9-EP was observed as the major metabolic pathway. The formation of 1-(hydroxymethyl)-phenanthrene was confirmed by reference to an authentic synthetic standard. However, formation of the bioactivated sulfate was not detected. Tetraols were also identified as signature metabolites of 1-MP and 9-EP, indicating that metabolic activation occurred via the diol-epoxide pathway. O-Monosulfonated-catechols were discovered as signature metabolites of the o-quinone pathway of metabolic activation of 1-MP and 9-EP, respectively. The identification of O-monosulfonated-catechols supports the metabolic activation of 1-MP and 9-EP by P450 and AKR isozymes followed by metabolic detoxification of the o-quinone through interception of redox cycling by phase II isozymes. The signature metabolites identified could be used as biomarkers of human exposure to 1-MP and 9-EP resulting from oil spills.

中文翻译：

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代表性的烷基化多环芳烃1-甲基菲和9-乙基菲的潜在代谢活化与人类肝癌（HepG2）细胞中的深水地平线漏油有关。

暴露于成岩性多环芳烃（PPAH）是与Deepwater Horizo​​n溢油有关的主要人类健康危害。烷基化菲是原油中含量最高的PPAH，可能污染食物链。我们描述了C _1-菲区域异构体1-甲基菲（1-MP）和C ₂的代谢-HepG2细胞中的-菲区域异构体9-乙基菲（9-EP）。通过HPLC-UV-荧光检测和LC-MS / MS鉴定代谢物的结构。观察到1-MP和9-EP的侧链羟基化是主要的代谢途径。参考真实的合成标准物确认了1-（羟甲基）菲的形成。然而，未检测到生物活化的硫酸盐的形成。四醇也被鉴定为1-MP和9-EP的标志性代谢产物，表明代谢活化是通过二醇-环氧途径发生的。发现O-单磺化邻苯二酚分别是1-MP和9-EP的代谢活化的O-醌途径的标志性代谢物。O的鉴定-单磺化-邻苯二酚支持P450和AKR同工酶对1-MP和9-EP的代谢活化，然后通过II期同工酶截留氧化还原循环，使邻醌的代谢解毒。鉴定出的特征代谢物可以用作人类因溢油而暴露于1-MP和9-EP的生物标志物。