9-Hydroxy-phenanthren-10-sulfat | 2564-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-Hydroxy-phenanthren-10-sulfat
• 英文别名: 9-Hydroxy-10-phenanthryl-sulfat
• CAS: 2564-21-8
• 化学式: C₁₄H₁₀O₅S
• 分子量: 290.296
• InChiKey: JZIVIEQNKBZKHB-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  菲醌 在 human recombinant sulfotransferase 1A₁ 、 6-氨基-9-[3,4-二羟基-5-[(羟基-磺基氧基-磷酰)氧基甲基]四氢呋喃-2-基]-嘌呤 、 magnesium chloride 、 1,4-二巯基-2,3-丁二醇 、 alamethicin 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 9-Hydroxy-phenanthren-10-sulfat
  参考文献：
  名称：

  Metabolism of a Representative Oxygenated Polycyclic Aromatic Hydrocarbon (PAH) Phenanthrene-9,10-quinone in Human Hepatoma (HepG2) Cells

  摘要：

  Exposure to polycyclic aromatic hydrocarbons (PAHs) in the food chain is the major human health hazard associated with the Deepwater Horizon oil spill. Phenanthrene is a representative PAH present in crude oil, and it undergoes biological transformation, photooxidation, and chemical oxidation to produce its signature oxygenated derivative, phenanthrene-9,10-quinone. We report the downstream metabolic fate of phenanthrene-9,10-quinone in HepG2 cells. The structures of the metabolites were identified by HPLC-UV-fluorescence detection and LC-MS/MS. O-mono-Glucuronosyl-phenanthrene-9,10-catechol was identified, as reported previously. A novel bis-conjugate, O-mono-methyl-O-mono-sulfonated-phenanthrene-9,10-catechol,was discovered for the first time, and evidence for both of its precursor mono conjugates was obtained. The identities of these four metabolites were unequivocally validated by comparison to authentic enzymatically synthesized standards. Evidence was also obtained for a minor metabolic pathway of phenanthrene-9,10-quinone involving bis-hydroxylation followed by O-mono-sulfonation. The identification of 9,10-catechol conjugates supports metabolic detoxification of phenanthrene-9,10-quinone through interception of redox cycling by UGT, COMT, and SULT isozymes and indicates the possible use of phenanthrene-9,10-catechol conjugates as biomarkers of human exposure to oxygenated PAH.

  DOI：

  10.1021/tx500031p