State Environmental Protection Key Laboratory of Environmental Pollution Health Risk Assessment, South China Institute of Environmental Sciences, Ministry of Ecology and Environment, Guangzhou 510655, China; Beijing Key Laboratory of Emerging Organic Contaminants Control, State Key Joint Laboratory of Environmental Simulation and Pollution Control, Collaborative Innovation Center for Regional Environmental Quality, School of Environment, Tsinghua University, Beijing 100084, China.
Beijing Key Laboratory of Emerging Organic Contaminants Control, State Key Joint Laboratory of Environmental Simulation and Pollution Control, Collaborative Innovation Center for Regional Environmental Quality, School of Environment, Tsinghua University, Beijing 100084, China; Department of Pharmacology, College of Medicine, the University of Arizona, Tucson, AZ 85721, United States.
Environ Int. 2020 May;138:105657. doi: 10.1016/j.envint.2020.105657. Epub 2020 Mar 30.
The present work aimed to discuss the enantiomeric occurrence of chiral pharmaceuticals including 5 parent compounds (PCs) metoprolol, propranolol, atenolol, venlafaxine and fluoxetine as well as 6 of their transformation products (TPs) in surface water in Beijing. Among which, 9 out of 11 were detected during the two sampling campaigns with N-O-Didesmethylvenlafaxine (NODDV) and α-hydroxymetoprolol confirmed in the catchment for the first time. Metoprolol acid (MTPA) was the most abundant up to 1508 ng L, followed by metoprolol and O-desmethylvenlafaxine (ODV). Most compounds showed 100% detection frequency or nearly, while norfluoxetine (the main metabolite of fluoxetine) and 4-hydroxypropranololone (one TP of propranolol) were not detected. Metoprolol (MTP) and venlafaxine (VFX) did not vary significantly between two sampling periods with mean concentrations of 280.7 and 22.9 ng L, respectively. Enantiomeric enrichment was observed for venlafaxine, metoprolol and NODDV, where R-venlafaxine was preferentially biotransformed than the S-form through O-desmethylation. Risk assessment indicated that fluoxetine and atenolol could pose harmful effects to aquatic organisms. This work provides enantiospecific profiles of pharmaceutically active compounds (PhACs), and extended the concept of applying the ratio of TPs vs. parent compound plus their enantiomeric traits for quantitative assessment of in situ biodegradation. Due to the considerable contribution by TPs (64% in present study) as well as the unexpected impacts from enantiomeric existence, the stereoselectivity of chiral pollutants during environmental process should be taken into account in future study. To the best of the authors' knowledge, it is the first comprehensive evaluation of chiral pharmaceuticals and transformation products at enantiomeric level in aquatic environment in China, which would facilitate better understanding of their environmental fate.
本研究旨在讨论包括 5 种母体化合物（PCs）（美托洛尔、普萘洛尔、阿替洛尔、文拉法辛和氟西汀）以及 6 种转化产物（TPs）在内的手性药物在北京市地表水环境中的对映体发生情况。在两次采样中，共检测到 11 种化合物中的 9 种，其中 N-O-去甲文拉法辛（NODDV）和 α-羟美托洛尔首次在集水区中被确认。美托洛尔酸（MTPA）的含量最高，达 1508ng/L，其次是美托洛尔和 O-去甲文拉法辛（ODV）。大多数化合物的检测频率接近 100%，但未检测到去甲氟西汀（氟西汀的主要代谢物）和 4-羟基普萘洛尔酮（普萘洛尔的一种 TP）。美托洛尔（MTP）和文拉法辛（VFX）在两个采样期之间没有显著差异，浓度分别为 280.7 和 22.9ng/L。文拉法辛、美托洛尔和 NODDV 表现出对映体富集，通过 O-去甲基化，R-文拉法辛优先被生物转化为 S-形式。风险评估表明，氟西汀和阿替洛尔可能对水生生物产生有害影响。本研究提供了手性药物的对映体特异性特征，并扩展了应用转化产物与母体化合物及其对映体特征的比值进行原位生物降解定量评估的概念。由于 TPs 的贡献相当大（本研究中为 64%）以及对映体存在的意外影响，在未来的研究中应考虑手性污染物在环境过程中的立体选择性。据作者所知，这是中国首次对手性药物及其在水环境中的转化产物进行全面的对映体水平评价，有助于更好地了解它们的环境命运。
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